CN106883278A - A kind of 3,5,7 trihydroxy 2 (4 hydroxy phenyl) ketone derivatives of chromene 4 - Google Patents
A kind of 3,5,7 trihydroxy 2 (4 hydroxy phenyl) ketone derivatives of chromene 4 Download PDFInfo
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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
Abstract
The invention discloses a kind of 3,5,7 trihydroxy 2 (4 hydroxy phenyl) ketone derivatives of chromene 4, its preparation method is as follows：1）Desmodium styracifolium dry seed is crushed, with petroleum ether degreasing, extracted with alcohol reflux again, extract solution is through being concentrated under reduced pressure into medicinal extract, plus distilled water is suspended, extracted with chloroform, water saturated n-butanol successively again, each several part extract is concentrated under reduced pressure, and obtains chloroform extract, n-butyl alcohol extract and water layer and stays excess；2）By ODS column chromatography for separation, silica gel column chromatography, CHCl3MeOH wash-outs, polyamide column chromatography and the purifying of hydroxypropyl sephadex are processed n-butyl alcohol extract, isolate the 3 of different structure, 5,7 trihydroxy 2 (4 hydroxy phenyl) ketone derivatives of chromene 4.The ketone derivatives Stability Analysis of Structures of of the invention 3,5,7 trihydroxy 2 (4 hydroxy phenyl) chromene 4, is isolated from Desmodium styracifolium seed, and with antioxidation, preparation process is simple, can be used as natural.
Description
Technical field
The present invention relates to a kind of 3,5,7- trihydroxies -2- (4- hydroxy phenyls)-benzopyran-4-one derivative.
Background technology
Desmodium styracifolium is the dry aerial parts of legume Desmodium styracifolium, is large cultivation medicinal material of Guangdong and Guangxi Provinces area, is
《Chinese Pharmacopoeia》Kind is included, the effect of with clearing heat and promoting diuresis, Tonglin Paishi, treatment kidney, liver, courage knot is widely used among the people
Stone, clinical efficacy is notable.The Desmodium styracifolium of early application is wild product, and with the continuous increase of medicinal material demand, medicine source is increasingly
Scarcity, product are cultivated at present has turned into the main source of commodity medicinal material.Desmodium styracifolium leans on seminal propagation, and medicinal material seed production is considerable.
But used as dis-medicinal part, in addition to annual seed selection is reserved seed for planting, seed still has a large amount of residues.Research on Desmodium styracifolium seed
It is concentrated mainly on seed seed superiority and quality standard aspect.Present invention research finds：Flavones is mainly contained in Desmodium styracifolium seed
Constituents, and its alcohol extract has antioxidation in vitro, and the chemical composition of Desmodium styracifolium seed is entered to be oriented to activity
Row system is separated, and can obtain a series of noval chemical compounds, expands the medicinal part of Desmodium styracifolium, is conducive to making full use of medicinal material
Resource.
The content of the invention
Derive it is an object of the invention to provide a kind of 3,5,7- trihydroxies -2- (4- hydroxy phenyls)-benzopyran-4-one
Thing.
Another object of the present invention is to provide a kind of 3,5,7- trihydroxies -2- (4- hydroxy phenyls)-benzopyran-4-one
The preparation method of derivative.
It is still another object of the present invention to provide a kind of 3,5,7- trihydroxies -2- (4- hydroxy phenyls)-benzopyran-4-one
The application of derivative.
The technical solution used in the present invention is：
One kind 3,5,7- trihydroxies -2- (4- hydroxy phenyls)-benzopyran-4-one derivative, its general structure is as follows：
Wherein, R1For-OH orR2For-OH, R3It is-H or-OH, and R1And R2It is asynchronously-OH.
Preferably, described derivative is
The preparation method of above-mentioned 3,5,7- trihydroxy -2- (4- hydroxy phenyls)-benzopyran-4-one derivative, including with
Lower step：
1) Desmodium styracifolium dry seed is crushed, with petroleum ether degreasing, then is extracted with alcohol reflux, extract solution is dense through depressurizing
Shorten medicinal extract into, plus distilled water is suspended, then extracted with chloroform, water saturated n-butanol successively, the decompression of each several part extract is dense
Contracting, obtains chloroform extract, n-butyl alcohol extract and water layer and stays excess；
2) by ODS column chromatography for separation, silica gel column chromatography, CHCl3- MeOH wash-outs, polyamide column chromatography and hydroxypropyl Portugal
Polysaccharide gel purifying is processed n-butyl alcohol extract, isolates the 3 of different structure, 5,7- trihydroxy -2- (4- hydroxy benzenes
Base)-benzopyran-4-one derivative.
The beneficial effects of the invention are as follows：3,5,7- trihydroxies -2- (4- hydroxy phenyls)-benzopyran-4-one of the invention
Derivant structure stabilization, is isolated from Desmodium styracifolium seed, and with good antioxidation, preparation process is simple,
Can be used as natural.
Brief description of the drawings
Fig. 1 is total reducing power test result that ascorbic acid, n-butyl alcohol extract, chloroform extract and water layer stay excess
Figure.
Specific embodiment
The present invention is made further explanation and description with reference to specific embodiment.
Embodiment：
1) preliminary extraction：
15kg Desmodium styracifolium dry seed is crushed, with petroleum ether degreasing, then with 95% alcohol reflux extraction 3 times, often
The time of secondary backflow is 3h, merges extract solution, is concentrated under reduced pressure into medicinal extract, plus appropriate distilled water is suspended, then uses chloroform, water to satisfy successively
The n-butanol of sum is repeatedly extracted, and each several part extract is concentrated under reduced pressure, and obtains chloroform extract 171g, n-butyl alcohol extract 664g
Excess 893g is stayed with water layer.
2) determination of total flavonoids：
1. the preparation of test sample solution
Chloroform extract 63.5mg, n-butyl alcohol extract 45.2mg, water layer are weighed respectively and stays excess 175mg, be placed in 3
In 25mL volumetric flasks, dissolved with 70% ethanol and be diluted to scale, shaken up, 4 DEG C of refrigerations are stand-by.
2. the preparation of reference substance solution
Kaempferol standard items 5.0mg is weighed, is placed in 50mL volumetric flasks, scale is dissolved and be diluted to 70% ethanol,
Shake up, 4 DEG C of refrigerations are stand-by.
3. the preparation of standard curve
Kaempferol mother liquor 0.4mL, 0.5mL, 0.6mL, 0.7mL, 0.8mL, 0.9mL are drawn respectively is placed in 6 10mL capacity
In bottle, the AlCl of 0.1moL/L is added3Solution 2mL, after shaking up placement 6min, the NaAc-HAc bufferings for adding pH=5.2 are molten
Liquid 1mL, with 70% ethanol constant volume, room temperature places 15min, then determines suction of each Kaempferol control sample at 417nm respectively
Luminosity, each Kaempferol control sample parallel determination 3 times.With Kaempferol control sample concentration (mg/mL) as abscissa (X),
Absorbance is ordinate (Y), draws standard curve, and regression equation is：Y=80.876X+0.0220 (R2=0.9997),
Linear dependence is good in 0.004~0.009mg/mL concentration ranges.
4. determination of total flavonoids
2mL steps chloroform extract 1., n-butyl alcohol extract and water layer are drawn respectively and stays excess, be placed in 3 10mL and hold
In measuring bottle, according to step 3. in method of testing test each sample absorbance, with sample concentration (mg/mL) as abscissa (X),
Absorbance is ordinate (Y), draws standard curve, and the general flavone content respectively carried in extraction is calculated according to standard curve.By meter
Calculate, chloroform extract, n-butyl alcohol extract and water layer stay the general flavone content in excess to be respectively：10.99mg/g、26.64mg/
G and 2.33mg/g.
3) antioxidation activity analysis：
1. total reducing power is determined
The sample solution that chloroform extract, n-butyl alcohol extract and water layer stay excess to be configured to various concentrations is taken, is respectively taken molten
Liquid 2.5mL, addition concentration is 0.2mol/L phosphate buffers (pH=6.6) 2.5mL, adds 1% potassium ferricyanide solution
2.5mL, is mixed, and the trichloroacetic acid 2.5mL that 10% is added after 20min is acted under 50 DEG C of water-baths, mix after under 4000r/m from
Heart 10min, takes supernatant 2.5mL and mixes with the ferric chloride in aqueous solution 0.5mL that concentration is 0.1%, room temperature reaction 10min, in
Mensuration absorbance under 700nm wavelength, ascorbic acid (Vc) is positive control.
Total reducing power of each sample is as shown in figure 1, as shown in Figure 1：Total reducing power size (absorbance of each sample
Its total reducing power of expression higher is stronger) it is as follows：Ascorbic acid>N-butyl alcohol extract>Chloroform extract>Water layer stays excess.
2. to the scavenging action of hydroxyl radical free radical (OH)
The sample solution that chloroform extract, n-butyl alcohol extract and water layer stay excess to be configured to various concentrations is taken, is respectively taken molten
Liquid 0.5mL, addition 7.5mmol/L Phen 0.5mL, 0.2mol/L PBS (pH=7.4) 1.0mL,
The FeSO of 7.5mmol/L4Solution 1mL, after fully mixing, adds 0.1% H2O2Solution 0.5mL, shakes up, and is placed in 37 DEG C of water-baths
Insulation 1h, the mensuration absorbance at 510nm, with ascorbic acid as positive control, is calculated：Clearance rate (%)=100% × (Ao-
As)/Ao, in formula, Ao is the absorbance of blank solution, and As is the absorbance of sample solution.
In the concentration range selected by experiment, each sample is presented good linear to the clearance rate (%) of OH with sample concentration
Relation, regression equation, R2And IC50Value is as shown in table 1.As shown in Table 1：Scavenging action of each sample to OH：Ascorbic acid>Just
Butanol extract>Chloroform extract>Water layer stays excess.
3. to superoxide anion (O2 -) scavenging action
Take that test tube is some, it is each to add Tris-HCl buffer solutions (pH=8.2) 4.5mL of 50mmol/L, then be separately added into not
The sample solution 1.0mL of homogenous quantities concentration, in 25 DEG C of water bath with thermostatic control 20min, adds 25mmol/L pyrogallol solution 0.1mL,
Mix in 25 DEG C of water bath with thermostatic control insulation 5min, 8mmol/L hydrochloric acid solution 1.0mL terminating reactions are added immediately, determined at 322nm
Absorbance, with Tris-HCl buffer solutions as reference liquid, ascorbic acid is positive control, is calculated：Clearance rate (%)=100% ×
[1- (As-Aso)/Ao], in formula, to add pyrogallol to be not added with sample solution, As is Ao plus pyrogallol also adds sample solution,
Aso is to be not added with pyrogallol plus sample solution.
In the concentration range selected by experiment, each sample is to O2 -Clearance rate (%) and sample concentration good linear is presented
Relation, regression equation, R2And IC50Value is as shown in table 1.As shown in Table 1：Each sample is to O2 -Scavenging action：Ascorbic acid>Just
Butanol extract>Chloroform extract>Water layer stays excess.
The each sample of table 1 is to OH and O2 -Scavenging action
BE：N-butyl alcohol extract, CE：Chloroform extract, WE：Water layer stays excess.
4. to the scavenging action of ABTS free radicals
Prepare ABTS storing solutions：Prepare the K of 2.45mmol/L2S2O8Solution, uses K2S2O8Solution dissolves ABTS, is made into
The ABTS storing solutions of 7mmol/L, room temperature, lucifuge stand 12~16h.By ABTS storing solutions with phosphate buffer (10mmol/L,
PH=7.4) dilute, make its absorbance that 0.700 ± 0.020 is reached at 734nm.The sample for pipetting different quality concentration respectively is molten
In test tube, the ABTS storing solutions of each addition 2mL, eddy oscillating 30s, lucifuge reacts 8min to liquid 1mL, is determined at 734nm and inhaled
Luminosity.With ascorbic acid as positive control, calculate：Clearance rate (%)=100% × (Ao-As)/Ao, in formula, Ao is stored up for ABTS
The absorbance of standby liquid, As is the absorbance of sample.
In the concentration range selected by experiment, each sample is presented good linear to the clearance rate (%) of ABTS with sample concentration
Relation, regression equation, R2And IC50Value is as shown in table 2.As shown in Table 2：Scavenging action of each sample to ABTS：Ascorbic acid>Just
Butanol extract>Chloroform extract>Water layer stays excess.
Scavenging action of each sample of table 2 to ABTS
BE：N-butanol extract, CE：Chloroform extract, WE：Water layer extract.
Different anti-oxidant experimental models show that the n-butyl alcohol extract of Desmodium styracifolium seed has obvious anti-oxidant work
Property, therefore separated as the chemical composition that active site carries out system.
4) system of active site is separated：
The preparation method of one kind 3,5,7- trihydroxies -2- (4- hydroxy phenyls)-benzopyran-4-one derivative, including with
Lower step：
1. n-butanol extract is taken appropriate, through ODS column chromatographies (MeOH-H2O, 1:9→10:0) separate, 29 are obtained after merging
Individual component Fr.1~Fr.29；
2. take Fr.16 and sequentially pass through silica gel column chromatography, CHCl3-MeOH(9:1→1:9) elute, 8 groups are obtained after merging
Divide Fr.16-1~Fr.16-8, take Fr.16-8 and sequentially pass through ODS column chromatographies (MeOH-H2O, 1:9→4:6), polyamide column chromatography
(MeOH-H2O, 1:9→10:0), Sephadex LH-20 purifying, obtains compound 1 (12mg) and compound 2 (10mg)；
3. take Fr.19 and sequentially pass through silica gel column chromatography, CHCl3-MeOH(9:1→6:4) elute, 10 groups are obtained after merging
Divide Fr.19-1~Fr.19-10, take Fr.19-10 and obtain compound 3 (5mg) through Sephadex LH-20 purifying；
4. take Fr.29 and sequentially pass through silica gel column chromatography (CHCl3- MeOH, 9:1→0:10), polyamide column chromatography (CHCl3-
MeOH, 9:1→6:4), Sephadex LH-20 purifying, obtains compound 4 (37mg).
Compound 1：Kaempferol -3-O- β-D- apiose (1 → 2)-β-D- glucopyranose -7-O- β-D- apiosides
Yellow powder.
The spectral data of compound 1 is as shown in table 3.
As shown in Table 3：
High resolution mass spectrum shows molecular weight [M+Na]+：M/z 735.1755 (calculated value 735.1748), molecular formula is
C31H36O19；
1H NMR (500MHz, DMSO-d6) in spectrum：δH12.66 (1H, s, OH), 6.75 (1H, d, J=2.0Hz, H-8),
6.38 (1H, d, J=1.9Hz, H-6) prompt for flavone A interannular position coupling proton signal；δH8.14 (2H, d, J=9.0Hz),
6.89 (2H, d, J=9.0Hz) prompt for flavones B ring AA ' BB ' systems；
In hsqc spectrum：Three anomeric proton δH5.63 (1H, d, J=3.4Hz), 5.62 (1H, d, J=7.7Hz), 5.35
(1H, d, J=1.4Hz) is respectively at three end group carbon δC107.2nd, 98.4,108.8 is related, points out to contain three in the compound
Sugar；
1H NMR、13In C NMR spectras：Anomeric proton δH5.63rd, 5.35 and end group carbon δC107.2nd, 108.8 is apiose
Type signal.Additionally, two secondary carbon signal δC74.7th, 73.9 and two quaternary carbon signal δC78.8th, 79.3 further demonstrate
Above-mentioned deduction.After the sour water solution of compound 1, hydrolysate is compared with standard items, it was demonstrated that the compound aglycon is Kaempferol, sugar is
Apiose and glucose.Anomeric proton δH5.63 coupling constant J=3.4Hz, shows that this apiose is configured as β-D- furan types
Apiose.3rd anomeric proton δH5.62 (J=7.7Hz) should be the anomeric proton signal of glucose；
In HMBC spectrums：Anomeric proton δH5.63 (H-1 " ") and δC162.5 (C-7) are related, point out an apiose to connect
It is connected to C-7；Anomeric proton δH5.62 (H-1 ") and δC133.3 (C-3) are related, point out glucose to be connected to C-3.To change
The carbon modal data of compound 1 and the compound Kaempferol -3-O- β for having reported-D-Glucose contrast, find the C-2 of compound 1 " change
Degree shifts to low field and moves 2.97ppm, and C-1 " chemical shift moves 2.43ppm to High-Field, thus infers second celery
Dish sugar is connected to C-2 "；
Therefore determine that compound 1 is：Kaempferol -3-O- β-D- apiose (1 → 2)-β-D- glucopyranose -7-O- β-D- celerys
Dish glucosides, structural formula is：
Compound 2：Kaempferol -3-O- β-D- glucopyranosyl -7-O- β-D- apiosides
Yellow powder.
The spectral data of compound 2 is as shown in table 3.
As shown in Table 3：
High resolution mass spectrum shows molecular weight [M+Na]+：M/z 603.1337 (calculated value 603.1326), molecular formula is
C26H28O15, it is 13 to calculate degree of unsaturation, and hydrochloric acid-magnesium powder reaction is positive, and prompts for flavone compound；
1H NMR (500MHz, DMSO-d6) in spectrum：δH6.39 (1H, d, J=2.0Hz) and 6.74 (1H, d, J=2.5Hz)
For the meta of flavone A ring couples proton signal, i.e. H-6 and H-8.δH8.08 (2H, d, J=9.0Hz) and 6.88 (2H, d, J=
9.0Hz) it is flavones B ring AA ' BB ' systems.δH5.47 (1H, d, J=7.5Hz) and 5.62 (1H, d, J=3.5Hz) anomeric protons
The signal prompt compound is containing sugar；After the sour water solution of compound 2, hydrolysate is compared with standard items, it was demonstrated that the compound aglycon
It is Kaempferol, sugar is apiose and glucose；
13C NMR (125MHz, DMSO-d6) and DEPT spectrum confirm compound in：Totally 26 carbon signals, including 3 methylene
Carbon, 13 methine carbons, 1 carbonyl carbon and 9 quaternary carbons.Ownership (the table of each proton signal and carbon signal is determined according to hsqc spectrum
5-1).There are 9 carbon signals in the high field region of carbon spectrum, add two end group carbon (δC100.8 and 107.1) it is speculated as double carbon oxygen sugar.
Three CH are shown in carbon spectrum2Signal, except δC60.8 is simultaneous δ outside glucose C-6 ' signalsC74.6 and 61.9
Two secondary carbon signals are the representative carbon signal of apiose, therefore demonstrate acid-hydrolyzed result, and glucose is contained in compound structure
And apiose.Sugar preferential conformation in, every H-2 ' for α keys sugar, when with aglycon formed β-glycosidic bond, wherein H-1 ' and H-2 '
It is α α coupled systems, J=6~9Hz, and one doublet of presentation.Glucose anomeric proton δ is understood by hydrogen spectrumH5.47(1H,d,J
=7.5Hz), therefore glucose is β-D configurations；
By apiose1H NMR and13C NMR datas and document[134]Compare, determine that the apiose in structure is β-D structures
Type.
In HMBC spectrums：The anomeric proton δ of glucoseHC-3 (δ on 5.47 (1H, d, J=7.5Hz) and flavones parent nucleusC
133.5) it is related, show that the end group of glucose is connected with 3-O of aglycon.The anomeric proton δ of apioseH5.62 (1H, d, J=
C-7 (δ 3.5Hz) and on flavones parent nucleusC162.5) it is related, show that the end group of apiose is connected with 7-O of aglycon.According to
Other coherent signals of HMBC spectrums demonstrate above-mentioned deduction；
Therefore determine that compound 2 is：Kaempferol -3-O- β-D- glucopyranosyl -7-O- β-D- apiosides, structural formula
For：
Spectral data (the in DMSO-d of the compound 1 and 2 of table 36, 500and 125MHz)
Compound 3：Kaempferol -7-O- β-D- apiosides
Yellow powder.
The spectral data of compound 3 is as shown in table 4.
As shown in Table 4：
High resolution mass spectrum shows molecular weight [M-H]-：M/z 417.0807 (calculated value 417.0822), molecular formula is
C20H18O10；
The spectral data of compound 3 is very close with compound 2, is only the absence of 3-O- β-D-Glucose, therefore determine compound 3
For：Kaempferol -7-O- β-D- apiosides, structural formula is：
Compound 4：2 "-(E)-p- coumaric acyl quercitins
Yellow powder.
The spectral data of compound 4 is as shown in table 4.
As shown in Table 4：
High resolution mass spectrum shows molecular weight [M-H]-：M/z 593.1273 (calculated value 593.1295), molecular formula is
C30H26O13, it is 18 to calculate degree of unsaturation, and hydrochloric acid-magnesium powder reaction is positive, and prompts for flavone compound；
1H NMR (500MHz, DMSO-d6) in spectrum：δH12.55 (1H, s), 6.41 (1H, d, J=2.0Hz) and 6.21
For 5,7 dihydroxy replace on (1H, d, J=2.0Hz) proton signal prompting flavone A ring.δH7.34 (1H, d, J=2.5Hz),
It is 3 ', 4 '-two on 7.30 (1H, dd, J=8.5,2.5Hz) and 6.89 (1H, d, J=8.5Hz) proton signals prompting flavones B rings
Hydroxyl replaces.δH5.50 (1H, d, J=1.5Hz), 5.43 (1H, dd, J=3.5,1.5Hz), 3.23-3.74 (3H, m) and
0.89 (3H, d, J=5.5Hz) proton signal points out the compound containing sugar.After the sour water solution of compound 4, by hydrolysate and standard
Product are compared, it was demonstrated that contain L- rhamnoses；
13C NMR (125MHz, DMSO-d6) and DEPT spectrums confirm totally 30 carbon signals in compound, including 1 methyl carbon,
16 methine carbons, 2 carbonyl carbons and 11 quaternary carbons.Ownership (the table 5- of each proton signal and carbon signal is determined according to hsqc spectrum
1)；
In HMBC spectrums, δH7.34 (1H, d, J=2.5Hz, H-2 ') and δC157.4 (C-2), 148.6 (C-4 '),
There are relevant peaks in 121.2 (C-6 ')；δH7.30 (1H, dd, J=8.5,2.5Hz, H-6 ') and δC157.4 (C-2), 115.7 (C-
2 '), there are relevant peaks in 148.6 (C-4 '), and the aglycon for illustrating the compound is Quercetin；
In HMBC spectrums, δH5.50 (1H, d, J=1.5Hz, H-1 ") and δCThere are relevant peaks in 133.4 (C-3), illustrate L- mouse
Lee's sugar is connected on C-3.δH7.56 (2H, d, J=8.5Hz, H-2 " ', 6 " ') and 6.79 (2H, d, J=8.5Hz, H-3 " ',
5 " ') prompting contains 1,4- substituted benzene rings.δH7.57 (1H, d, J=16.0Hz, H-7 " ') and 6.39 (1H, d, J=16.0Hz,
H-8 " ') it is trans olefins structure fragment.In HMBC spectrums, δHH-7 " ' and δC130.5 (C-2 " '), 114.1 (C-8 " '), 165.9
(C-9 " ') there are relevant peaks；H-8 " ' and 125.1 (C-1 " ') and C-9 " ' there are relevant peaks.To sum up, it is known that contain in compound
(E)-p-coumaroyl structure fragments[135].H-2 in 3-O- rhamanopyranosyls " (5.43,1H, dd, J=3.5,1.5Hz) proton
Signal and C-2 " (71.6) signal speculates that coumaroyl fragments are connected to the C-2 of rhamnose to low field offset, thus " on position；
In HMBC spectrums, H-1 " and C-3, C-4 " (δC68.6), C-5 " (δC71.6) there are relevant peaks, H-2 " and C-4 ", C-
9 " ' there are relevant peaks；
In sum, it was demonstrated that compound 4 is：2 "-(E)-p- coumaric acyl quercitins, structural formula is：
Spectral data (the in DMSO-d of the compound 3 and 4 of table 46, 500and 125MHz)
Above-described embodiment is the present invention preferably implementation method, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other it is any without departing from Spirit Essence of the invention and the change, modification, replacement made under principle, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (4)
1. one kind 3,5,7- trihydroxy -2- (4- hydroxy phenyls)-benzopyran-4-one derivative, it is characterised in that：Its structure is led to
Formula is as follows：
Wherein, R1For-OH orR2For-OH, R3It is-H or-OH, and R1And R2It is asynchronously-OH.
2. according to claim 13,5,7- trihydroxy -2- (4- hydroxy phenyls)-benzopyran-4-one derivative, it is special
Levy and be：Described derivative is：
3. the preparation of 3,5,7- trihydroxies -2- (4- the hydroxy phenyls)-benzopyran-4-one derivative described in claim 1 or 2
Method, it is characterised in that：Comprise the following steps：
1) Desmodium styracifolium dry seed is crushed, with petroleum ether degreasing, then is extracted with alcohol reflux, extract solution is through being concentrated under reduced pressure into
Medicinal extract, plus distilled water is suspended, then is extracted with chloroform, water saturated n-butanol successively, and each several part extract is concentrated under reduced pressure, and obtains
Excess is stayed to chloroform extract, n-butyl alcohol extract and water layer；
2) by ODS column chromatography for separation, silica gel column chromatography, CHCl3- MeOH wash-outs, polyamide column chromatography and hydroxypropyl glucan are solidifying
Glue purification is processed n-butyl alcohol extract, isolates the 3 of different structure, 5,7- trihydroxy -2- (4- hydroxy phenyls)-benzo
Pyrans -4- ketone derivatives.
4. 3,5,7- trihydroxies -2- (4- the hydroxy phenyls)-benzopyran-4-one derivative described in claim 1 or 2 is used to make
The application of standby antioxidant.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107652259A (en) * | 2017-10-31 | 2018-02-02 | 桂林纽泰生物科技有限公司 | A kind of method that Quercetin is extracted from Desmodium styracifolium |
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| CN109912611A (en) * | 2019-03-25 | 2019-06-21 | 河南湾流生物科技有限公司 | A kind of benzo pyran cosmetic and preparation method thereof with removing free radical effect |
| CN109912611B (en) * | 2019-03-25 | 2021-07-20 | 浙江瑀美生物科技有限公司 | Benzopyran cosmetic auxiliary material with effect of removing free radicals and preparation method thereof |
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