CN104974018B - Compound extracted from Chinese medicine Ramulus Et Folium Pithecellobii Lucidi and application thereof - Google Patents
Compound extracted from Chinese medicine Ramulus Et Folium Pithecellobii Lucidi and application thereof Download PDFInfo
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- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
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- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
Abstract
The invention belongs to pharmaceutical technology field, relate to from pulse family Ramulus Et Folium Pithecellobii Lucidi platymiscium Ramulus Et Folium Pithecellobii Lucidi (Pithecellobium clypearia Benth.The compound separated is extracted in), chemistry is entitled: 5 pi-allyl 5'(2 hydroxypropyls) [1,1' biphenyl] 2,2' glycol, 5 pi-allyl 5'(2,3 dihydroxy 1 methoxy-propyls) [1,1 biphenyl] 2,2' glycol, 1 (3' methoxyl group, 4' hydroxy phenyl) 3 (2'', 6'' dimethoxy 4'' hydroxy phenyl) propane 2 alcohol.Be by by Ramulus Et Folium Pithecellobii Lucidi crude extract through silica gel repeatedly, ODS column chromatography, three noval chemical compounds of HPLC isolated.Through the measurement result of ABTS radical scavenging activity, show that three compounds are respectively provided with good antioxidant activity, treatment and the medicine of prevention radical pair human body destruction relevant disease can be prepared.
Description
Technical field:
The invention belongs to pharmaceutical technology field, relate to three noval chemical compounds and preparation method thereof in Ramulus Et Folium Pithecellobii Lucidi, the invention still further relates to the application in preparing anti-oxidation medicine of the described noval chemical compound.
Background technology:
Free radical is the hazardous compound produced in body oxidation reaction, has strong oxidizing property.What our living things system mainly ran into is oxygen-derived free radicals, such as ultra-oxygen anion free radical, hydroxy radical, fat oxygen-derived free radicals, nitrogen dioxide and nitric oxide free radical.Plus hydrogen peroxide, singlet oxygen and ozone, it is generally called active oxygen.Too much reactive oxygen free radical can damage tissue and the cell of body, and then causes chronic disease such as heart disease, senile dementia, parkinson disease, tumor and aging effect.The reactive oxygen free radical a kind of oxidizing process of infringement to human body, therefore, the infringement of free radical to be reduced, must realize from antioxidation.Three compounds involved in the present invention are by preparing Ramulus Et Folium Pithecellobii Lucidi extract, for having no three noval chemical compounds of report, there is good free radical scavenging activity, thus reach antioxidative effect, be three lead compound with the biggest potential value.
Summary of the invention:
An object of the present invention is to find new antioxidation prodrug from Ramulus Et Folium Pithecellobii Lucidi twig and leaf, the two of the purpose of the present invention are to provide the extraction of this noval chemical compound, preparation method, and study their antioxidation biology activity and medical usage, the three of the purpose of the present invention are to provide the Structural Identification method of this noval chemical compound, the four of the purpose of the present invention to be the application providing three noval chemical compounds in preparing anti-oxidation medicine.
Three noval chemical compounds 5-pi-allyl-5'-(2-hydroxypropyl) [1 with antioxidant activity of the present invention, 1'-biphenyl]-2,2'-glycol, 5-pi-allyl-5'-(2,3-dihydroxy-1-methoxy-propyl) [1,1-biphenyl]-2,2'-glycol, and 1-(3'-methoxyl group, 4'-hydroxy phenyl)-3-(2 "; 6 "-dimethoxy-4 ' "-hydroxy phenyl) propane-2-alcohol, its structure is as follows:
The extraction of three noval chemical compounds of the present invention, preparation method are as follows:
(1) dry Ramulus Et Folium Pithecellobii Lucidi twig and leaf are taken, with 60～75% alcohol reflux, total extractum is obtained after united extraction liquid concentrating under reduced pressure, after total extractum use water suspendible, through D101 macroporous resin respectively with water and volume fraction 25%～the ethanol water elution of 35%, 55%～65%, 85%～95%, 85%～95% ethanol elution thing uses fast decompression column chromatography, with dichloromethane/chloroform-methanol system 50:1～2:1 gradually eluting, obtain 15～20 flow points, know through silica gel thin-layer chromatography inspection, flow point is merged into A1～A5.
(2) flow point A1 (eluted fraction of 50:1～30:1) is again through ODS column chromatography, with methanol-water system 40%～90% gradually eluting, obtains 12～18 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into F1～F3.Flow point F2 through silica gel column chromatography, with dichloromethane/chloroform-methanol system 30:1～1:1 gradually eluting, obtains 20～30 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into B1～B7.HPLC method is utilized to prepare compound 1 and 3 with methanol-water (50%～65%) in B2～B6 for flowing.
(3) flow point A2 (eluted fraction of 30:1～15:1) is again through ODS column chromatography, with methanol-water system 40%～80% gradually eluting, obtains 15～20 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into C1～C5.Flow point C2 through silica gel column chromatography, with dichloromethane/chloroform-methanol system 15:1～1:1 gradually eluting, obtains 20～30 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into D1～D5.HPLC method is utilized to prepare compound 2 with methanol-water (50%～65%) in D2～D4 for flowing.
The described reflux, extract, that is extracted as, extracts 3～5 times, each 2～3 hours.
Described preparation method, it is characterised in that the ratio of the described methanol-water for HPLC is 50%～65%.
Described Ramulus Et Folium Pithecellobii Lucidi refers to pulse family Ramulus Et Folium Pithecellobii Lucidi platymiscium Ramulus Et Folium Pithecellobii Lucidi (Pithecellobium clypearia Benth.).
Specifically: the preparation method of described three compounds is as follows:
Take dry Ramulus Et Folium Pithecellobii Lucidi twig and leaf 15～19kg, with the 60 of 5～7 times amount～75% industrial alcohol reflux, extract, 3～5 times, each 2～3 hours, total extractum 1.5～2.0kg is obtained after united extraction liquid concentrating under reduced pressure, total extractum is with after 8～10L water suspendibles, through D101 macroporous resin respectively with water and the ethanol water elution of volume fraction 30%, 60%, 95%, the 30% layer of dry extract 90～110g obtained, 60% layer of dry extract 300～400g, 95% layer of dry extract 180～210g, water layer dry extract 290～320g.95% ethanol elution thing uses fast decompression column chromatography, with methylene chloride-methanol system 50:1～2:1 gradually eluting, obtains 15～20 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into A1～A5.
Flow point A1 (40～60g) through ODS column chromatography, with methanol-water system 40%～90% gradually eluting, obtains 12～18 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into F1～F3.Flow point F2 through silica gel column chromatography, with methylene chloride-methanol system 30:1～1:1 gradually eluting, obtains 20～30 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into B1～B7.HPLC method is utilized to prepare compound 1 and 3 with methanol-water in B2～B6 for flowing.
Flow point A2 (40～60g) through ODS column chromatography, with methanol-water system 40%～80% gradually eluting, obtains 15～20 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into C1～C5.Flow point C2 through silica gel column chromatography, with methylene chloride-methanol system 15:1～1:1 gradually eluting, obtains 20～30 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into D1～D5.HPLC method is utilized to prepare compound 2 with methanol-water in D2～D4 for flowing.
Three noval chemical compounds of the present invention have preferable antioxidant activity.ABTS free radical scavenging activity test method is as follows:
1. experiment material
1.1 by test product: compound
1.2 reagent: ABTS (Chinese blue chemical reagents corporation), Trolox (Chinese blue chemical reagents corporation), PBS (Silarbio company)
2. experimental technique
2.1 drug treating
The dissolving of medicine
Compound and Trolox dehydrated alcohol are configured to 100,50,10,5,15 concentration of μ g ml；PBS distilled water is configured to 0.01M；The ABTS PBS prepared is configured to 3.84mg mL-1, then with 0.66mg mL-1Potassium persulfate solution 1:1 mix homogeneously by volume, room temperature lucifuge place 12-16h, i.e. generate ABTS.+, then with PBS diluted 10 times stand-by.
2.1 experimental implementation
Add variable concentrations sample solution (1,5,10,50,100 μ g mL-1) 100 μ L and the ABTS prepared.+Solution 150 μ L is in 96 hole ELISA Plate, concussion 1min, place 30min, under 734nm, its absorbance (S) is measured by microplate reader, measure sample P BS matched group absorbance (SB), ABTS negative control group absorbance (C) and dehydrated alcohol PBS blank group absorbance (CB) simultaneously.With Trolox as positive control, free radical scavenging activity calculated as below: suppression ratio (ABTS.+Clearance rate)=[1-(S-SB)/(C-CB)] × 100%
2.2 statistical procedures methods
All data use SPSS (16.0) statistical packages to test analysiss, result employing IC50Value assesses sample antioxidant activity.
2.3 experimental result
Determining the ABTS free radical scavenging activity of compound 1-3, result shows that three compounds all have good free-radical scavenging activity, the IC of compound 1-350Value is respectively 14.941,7.652,9.772 μ g mL-1, the IC of positive control Trolox50Value is 14.152 μ g mL-1.Can be seen that, in addition to activity and the positive drug of compound 1 are suitable, the activity of compound 2 and 3 is all good than positive drug.
Three noval chemical compounds of isolated from Ramulus Et Folium Pithecellobii Lucidi involved in the present invention, are respectively provided with good antioxidant activity, are three lead compound with the biggest potential value.
Preparation method of the present invention is simple, favorable reproducibility, and DNA purity is high.The compound obtained has good antioxidant activity effect.
Accompanying drawing explanation
Fig. 1 is 11H-NMR
Fig. 2 is 113C-NMR
Fig. 3 is the HSQC of 1
Fig. 4 is the HMBC of 1
Fig. 5 is 21H-NMR
Fig. 6 is 213C-NMR
Fig. 7 is the HSBC of 2
Fig. 8 is the HMBC of 2
Fig. 9 is 31H-NMR
Figure 10 is 313C-NMR
Figure 11 is the HSBC of 3
Figure 12 is the HMBC of 3.
Detailed description of the invention:
Preparation embodiment 1
Take dry Ramulus Et Folium Pithecellobii Lucidi twig and leaf 19kg, by the 70% industrial alcohol reflux, extract, 3 times of 6 times amount, each 3 hours, total extractum 1.9kg is obtained, after total extractum 10L water suspendible, through D101 macroporous resin respectively with water and the ethanol water elution of volume fraction 30%, 60%, 95% after united extraction liquid concentrating under reduced pressure, the water layer dry extract 310g obtained, 30% layer of dry extract 107g, 60% layer of dry extract 380g, 95% layer of dry extract 200g.95% ethanol elution thing uses fast decompression column chromatography, with methylene chloride-methanol system 50:1,30:1,15:1,8:1,5:1,2:1 gradually eluting, obtains 18 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into A1～A5.
Flow point A1 (50g) through ODS column chromatography, with methanol-water system 40%, 50%, 60%, 70%, 80%, 90% gradually eluting, obtains 18 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into F1～F3.Flow point F2, again through silica gel column chromatography, with methylene chloride-methanol system 30:1,15:1,8:1,5:1,3:1,1:1 gradually eluting, obtains 24 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into B1～B7.Utilizing HPLC method to prepare compound 1 with methanol-water system 65% in B5 for flowing, methanol-water system 60% prepares compound 3 for flowing in B4.
Flow point A2 (56g) through ODS column chromatography, with methanol-water system 40%, 50%, 60%, 70%, 80% gradually eluting, obtains 20 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into C1～C5.Flow point C2, again through silica gel column chromatography, with methylene chloride-methanol system 15:1,8:1,5:1,3:1,2:1,1:1 gradually eluting, obtains 24 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into D1～D5.HPLC method is utilized to prepare compound 2 with methanol-water system 60% in D2 for flowing.
Preparation embodiment 2
Take dry Ramulus Et Folium Pithecellobii Lucidi twig and leaf 17kg, by the 75% industrial alcohol reflux, extract, 4 times of 5 times amount, each 2 hours, total extractum 1.7kg is obtained, after total extractum 9L water suspendible, through D101 macroporous resin respectively with water and the ethanol water elution of volume fraction 30%, 60%, 95% after united extraction liquid concentrating under reduced pressure, the water layer dry extract 300g obtained, 30% layer of dry extract 100g, 60% layer of dry extract 360g, 95% layer of dry extract 190g.95% ethanol elution thing uses fast decompression column chromatography, with methylene chloride-methanol system 50:1,30:1,15:1,8:1,5:1,3:1 gradually eluting, obtains 18 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into A1～A5.
Flow point A1 (40g) through ODS column chromatography, with methanol-water system 40%, 50%, 60%, 70%, 80%, 90% gradually eluting, obtains 16 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into F1～F3.Flow point F2, again through silica gel column chromatography, with methylene chloride-methanol system 35:1,15:1,8:1,5:1,3:1,1:1 gradually eluting, obtains 28 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into B1～B7.Utilizing HPLC method to prepare compound 1 with methanol-water system 65% in B4 for flowing, methanol-water system 63% prepares compound 3 for flowing in B3.
Flow point A2 (45g) through ODS column chromatography, with methanol-water system 40%, 50%, 60%, 70%, 80% gradually eluting, obtains 15 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into C1～C5.Flow point C2, again through silica gel column chromatography, with methylene chloride-methanol system 15:1,8:1,5:1,3:1,2:1,1:1 gradually eluting, obtains 25 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into D1～D5.HPLC method is utilized to prepare compound 2 with methanol-water system 65% in D3 for flowing.
Preparation embodiment 3
Take dry Ramulus Et Folium Pithecellobii Lucidi twig and leaf 15kg, by the 65% industrial alcohol reflux, extract, 5 times of 7 times amount, each 2 hours, total extractum 1.5kg is obtained, after total extractum 8L water suspendible, through D101 macroporous resin respectively with water and the ethanol water elution of volume fraction 30%, 60%, 95% after united extraction liquid concentrating under reduced pressure, the water layer dry extract 290g obtained, 30% layer of dry extract 90g, 60% layer of dry extract 330g, 95% layer of dry extract 180g.95% ethanol elution thing uses fast decompression column chromatography, with methylene chloride-methanol system 35:1,20:1,10:1,5:1,3:1,2:1 gradually eluting, obtains 16 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into A1～A5.
Flow point A1 (42g) through ODS column chromatography, with methanol-water system 40%, 50%, 60%, 70%, 80% gradually eluting, obtains 15 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into F1～F3.Flow point F2, again through silica gel column chromatography, with methylene chloride-methanol system 30:1,15:1,8:1,5:1,2:1,1:1 gradually eluting, obtains 27 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into B1～B7.Utilizing HPLC method to prepare compound 1 with methanol-water system 64% in B5 for flowing, methanol-water system 62% prepares compound 3 for flowing in B4.
Flow point A2 (43g) through ODS column chromatography, with methanol-water system 40%, 50%, 60%, 70%, 80% gradually eluting, obtains 15 flow points again, knows through silica gel thin-layer chromatography inspection, flow point is merged into C1～C5.Flow point C2, again through silica gel column chromatography, with methylene chloride-methanol system 20:1,10:1,5:1,3:1,2:1,1:1 gradually eluting, obtains 26 flow points, knows through silica gel thin-layer chromatography inspection, flow point is merged into D1～D5.HPLC method is utilized to prepare compound 2 with methanol-water system 60% in D2 for flowing.
The structure elucidation of three noval chemical compounds of the present invention:
Experimental example 1:
Compound 1 (6mg) is yellow oil (methanol)；High-resolution electron spray ion massspectrum (HR-ESI-MS) provides quasi-molecular ion peak m/z 307.1319 [M+Na]+(cal.307.1305), in conjunction with1H NMR、13C H NMR spectroscopy, determines that molecular formula is C18H20O3；UV (MeOH) is at λmax217,292nm have absorption maximum, illustrate to there is phenyl ring skeleton；IR (KBr) is at 3426cm-1There is absorption, illustrate to there is hydroxyl, at 1495cm-1And 820cm-1There is absorption, illustrate to there is phenyl ring skeleton；?1H H NMR spectroscopy (400Hz, DMSO-d6null,ppm,J in Hz) in，δ: 6.94 (2H,s,H-6/H-6'),6.93(2H,overlaped,H-4/H-4'),6.76(2H,overlaped,H-3/H-3') it is two 1,3,6 proton signals that 4-phenyl ring replaces,δ: 5.94 (1H,ddt,J=17.0,9.6,6.4Hz,H-8),5.06(1H,br.d,J=17.0Hz,H-9a),5.00(1H,br.d,J=9.6Hz,H-9b) it is three proton signals on a terminal double bond,δ: 3.74 (1H,m,H-8') it is 2 proton signals on company's Oxymethylene,δ: 3.27 (2H,d,J=6.4Hz,H-7),2.61(1H,dd,J=5.8,13.2Hz,H-7'a),2.45(1H,dd,J=6.5,13.2Hz,H-7'b) it is two methene proton signals being connected on phenyl ring,δ: 1.02 (3H,d,J=5.7Hz,9'-CH3) it is a methyl proton signal；?13C H NMR spectroscopy (100MHz, DMSO-d6, ppm) 18 carbon signals are given in, including 12 aromatic carbon signals δ: 126.8 (C-1), 153.6 (C-2), 116.2 (C-3), 128.3 (C-4), 129.8 (C-5), 131.7 (C-6), 126.3 (C-1'), 153.8 (C-2'), 116.6 (C-3'), 129.3 (C-4'), 129.8 (C-5'), 132.5 (C-6'), two double key carbon signals δ: 138.9 (C-8), 115.6 (C-9), one company's oxygen carbon signal δ: 68.1 (C-8') and three alkyl carbon signals δ: 45.2 (C-7'), 23.5 (C-9'), 39.3 (C-7).In HMBC composes, H-7 to C-4, C-5, C-6, C-8, C-9 have relevant, and display pi-allyl is connected on C-5, H-7'a and H-7'b has relevant to C-4', C-5', C-6', C-8', C-9', shows that another three carbochain is connected on C-5'.Be can determine that the structure of compound by above derivation, molecular formula is C18H20O3, consistent with the molecular formula given by HR-ESI-MS.Through scifinder literature search, it is a noval chemical compound having no report, named 5-pi-allyl-5'-(2-hydroxypropyl) [1,1'-biphenyl]-2,2'-glycol.The hydrocarbon home to return to of compound 1 and HMBC are correlated with and see Table.1.
Experimental example 2:
Compound 2 (9mg) is yellow oil (methanol)；High-resolution electron spray ion massspectrum (HR-ESI-MS) provides quasi-molecular ion peak m/z 353.1360 [M+Na]+(calcd for C19H22NaO5, 353.1359), in conjunction with1H NMR、13C H NMR spectroscopy, determines that molecular formula is C19H22O5；IR (KBr) is at 3425cm-1There is absorption, illustrate to there is hydroxyl, at 1496cm-1And 826cm-1There is absorption, illustrate to there is phenyl ring skeleton；UV (MeOH) is at λmax220,289nm have absorption maximum, further illustrate and there is phenyl ring skeleton；According to1H NMR and13C H NMR spectroscopy can be seen that compound 2 and compound 1 have identical architectural feature, three carbochains being simply connected on C-5' are otherwise varied, can release in conjunction with HMBC spectrum, C-7' has connected a methoxyl group, C-9' is become methylol by methyl, and other signal is all identical with compound 1.Be can determine that the structure of compound by above derivation, this is also C with compound 2 molecular formula19H22O5It is consistent, through scifinder literature search, is a noval chemical compound having no report, named 5-pi-allyl-5'-(2,3-dihydroxy-1-methoxy-propyl) [1,1-biphenyl]-2,2'-glycol.The hydrocarbon home to return to of compound 2 and HMBC are correlated with and see Table.1.
Experimental example 3:
Compound 3 (8mg) is yellow oil (methanol)；High-resolution electron spray ion massspectrum (HR-ESI-MS) provides quasi-molecular ion peak m/z 357.1309 [M+Na]+(calcd for C18H22NaO6, 357.1309), in conjunction with1H NMR、13C H NMR spectroscopy, determines that molecular formula is C18H22O6；IR (KBr) is at 3425cm-1There is absorption, illustrate to there is hydroxyl, at 1515cm-1And 817cm-1There is absorption, illustrate to there is phenyl ring skeleton；?1H NMR composes (400Hz, DMSO-d6, ppm, J in Hz) in, δ: 6.68 (1H, d, J=1.8Hz, H-2'), 6.62 (1H, d, J=8.0Hz, H-5'), 6.49 (1H, dd, J=1.8,8.00Hz, H-6'), 6.04 (2H, s, H-3 ", H-5 ") it is 5 proton signals on two phenyl ring, δ: 3.71 (3H, s, 3'-OCH3), 3.68 (3H, s; 2 "-OCH3), 3.67 (3H, s, 6 "-OCH3) it is three methoxyl group proton signals；?13C H NMR spectroscopy (100MHz, DMSO-d6null,Ppm) 18 carbon signals are given in，Including 12 aromatic carbon signals δ: 131.4 (C-1'),113.9(C-2'),147.5(C-3'),144.9(C-4'),115.5(C-5'),121.8(C-6'),106.6(C-1”),159.5(C-2”),90.4(C-3”),157.4(C-4”),94.4(C-5”),159.3(C-6”),Three methoxyl group carbon signals δ: 56.0 (3'-OCH3),55.9(2”-OCH3),55.3(6”-OCH3)，One company's oxygen carbon signal δ: 72.3 (C-2)，Two alkyl carbon signals δ: 31.5 (C-3),42.8(C-1).Determine the structure of this compound in conjunction with HSQC and HMBC spectrum, be also C with compound 3 molecular formula18H22O6It is consistent, through scifinder literature search, is a noval chemical compound having no report, and named 1-(3'-methoxyl group, 4'-hydroxy phenyl)-3-(2 ", 6 "-dimethoxy-4 ' "-hydroxy phenyl) propane-2-alcohol.The hydrocarbon home to return to of compound 3 and HMBC are correlated with and see Table.1.
Table 1 compound 1-3's1H、13C NMR data
Claims (9)
1. following compound shown in structure:
。
2. the preparation method of compound as claimed in claim 1, it is characterised in that realized by following steps:
(1) dry Ramulus Et Folium Pithecellobii Lucidi twig and leaf are taken, with 60～75% alcohol reflux, total extractum is obtained after united extraction liquid concentrating under reduced pressure, after total extractum use water suspendible, through D101 macroporous resin respectively with water and volume fraction 25%～the ethanol water elution of 35%, 55%～65%, 85%～95%, 85%～95% ethanol elution thing uses fast decompression column chromatography, with dichloromethane/chloroform-methanol system 50:1～2:1 gradually eluting, obtain 15～20 flow points, know through silica gel thin-layer chromatography inspection, flow point is merged into A1～A5；
(2) the eluted fraction A1 of 50:1～30:1 is again through ODS column chromatography, with methanol-water system 40%～90% gradually eluting, obtain 12～18 flow points, know through silica gel thin-layer chromatography inspection, flow point is merged into F1～F3, flow point F2 is again through silica gel column chromatography, with dichloromethane/chloroform-methanol system 30:1～1:1 gradually eluting, obtain 20～30 flow points, know through silica gel thin-layer chromatography inspection, flow point is merged into B1～B7 and utilizes HPLC method to prepare compound 1 and 3 with methanol-water in B2～B6 for flowing；
(3) the eluted fraction A2 of 30:1～15:1 is again through ODS column chromatography, with methanol-water system 40%～80% gradually eluting, obtain 15～20 flow points, know through silica gel thin-layer chromatography inspection, flow point is merged into C1～C5, flow point C2 is again through silica gel column chromatography, with dichloromethane/chloroform-methanol system 15:1 ~ 1:1 gradually eluting, obtain 20～30 flow points, know through silica gel thin-layer chromatography inspection, flow point is merged into D1～D5, utilizes HPLC method to prepare compound 2 with methanol-water in D2～D4 for flowing.
Preparation method the most according to claim 2, it is characterised in that be extracted as reflux, extract, described in:, extracts 3～5 times, each 2～3 hours.
Preparation method the most according to claim 2, it is characterised in that the ratio of the described methanol-water for HPLC is 50%-65%.
Preparation method the most according to claim 2, it is characterised in that: described Ramulus Et Folium Pithecellobii Lucidi refer to pulse family Ramulus Et Folium Pithecellobii Lucidi platymiscium Ramulus Et Folium Pithecellobii Lucidi (Pithecellobium clypearia Benth.)。
6. pharmaceutical composition, it is characterised in that comprise the compound described in claim 1 and pharmaceutically acceptable carrier.
7. the compound described in claim 1 or the pharmaceutical composition described in claim 6 application in preparing anti-oxidation medicine.
Application the most according to claim 7, it is characterised in that described anti-oxidation medicine is the medicine having and removing ABTS free radical ability.
Application the most according to claim 7, it is characterised in that described anti-oxidation medicine is and the medicine of radical pair human body destruction relevant disease.
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| KR102175732B1 (en) * | 2019-04-03 | 2020-11-09 | 연세대학교 산학협력단 | ANTIVIRAL COMPOSITION COMPRISING COMPOUND ISOLATED FROM Lindera glauca |
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| CN109946397A (en) * | 2019-03-26 | 2019-06-28 | 广州莱泰制药有限公司 | A kind of pithecellobium clypearia method of inspection |
| CN110305181B (en) * | 2019-06-28 | 2021-06-01 | 沈阳药科大学 | Triterpene compound in pithecellobium clypearia, preparation and application thereof |
| CN110483462B (en) * | 2019-08-22 | 2021-06-18 | 沈阳药科大学 | Polyphenol compound with neuroprotective activity and preparation method thereof |
| CN111850080B (en) * | 2020-08-24 | 2021-10-12 | 广东态合堂实业有限公司 | Preparation method of pithecellobium clypearia polypeptide and preparation method of pithecellobium clypearia polypeptide liposome |
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| EP1654210B1 (en) * | 2003-08-14 | 2008-07-30 | Thomas Szekeres | Stilbene derivatives and their use in medicaments |
| CN1305870C (en) * | 2004-10-29 | 2007-03-21 | 广州莱泰制药有限公司 | Novel flavane derivative and its preparation method and uses |
| CN100548321C (en) * | 2004-12-29 | 2009-10-14 | 广州莱泰医药科技有限公司 | Ramulus Et Folium Pithecellobii Lucidi extract is used to prepare the application of Claritin, food and cosmetics |
| CN100544746C (en) * | 2006-02-21 | 2009-09-30 | 广州莱泰医药科技有限公司 | The new purposes of Ramulus Et Folium Pithecellobii Lucidi extract |
| CN1817873A (en) * | 2006-02-21 | 2006-08-16 | 广州莱泰制药有限公司 | Flavane compound and use thereof |
| US8524782B2 (en) * | 2008-07-23 | 2013-09-03 | Laurus Labs Private Limited | Key intermediate for the preparation of Stilbenes, solid forms of Pterostilbene, and methods for making the same |
| CN101596229B (en) * | 2009-04-15 | 2011-06-22 | 广州莱泰制药有限公司 | Pithecellobium clypearia extract and quality control method of preparation thereof |
| CN103385912B (en) * | 2013-07-24 | 2015-06-17 | 中山大学 | Pithecellobium clypearia extracts and application of extract in preparation of medicines for treating methicillin-resistant staphylococcus aureus |
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