CN101538297A - Preparation method of high-purity monomer flavone and general flavone contained in capsella bursa-pastoris and application of general flavone - Google Patents
Preparation method of high-purity monomer flavone and general flavone contained in capsella bursa-pastoris and application of general flavone Download PDFInfo
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Abstract
The invention relates to a preparation method of a general flavone and several high-purity monomer flavones contained in capsella bursa-pastoris and the application of the general flavone on angiocardiopathy, the general flavone and the several high-purity monomer flavones are flavonoid compounds from the capsella bursa-pastoris. The preparation method of the general flavone comprises the following steps: medicinal material extraction and general flavone preparation, i.e. dry herbs of the capsella bursa-pastoris are extracted by alcohol reflux, ultrasound or cold soaking and then put onto a column by using macroporous resins and eluted by 30-90 percent of the alcohol, and alcohol eluate is collected and then concentrated and dried to obtain the general flavone with the content of more than 60 percent. The general flavone prepared by the method can be used for preparing drugs for treating the angiocardiopathy. A preparation method of the high-purity monomer flavones comprises the medicinal material extraction, separation and purification. The preparation method is simple, practical, fast and convenient, has low cost and is suitable for industrialized production.
Description
Technical field
The present invention relates to field of medicaments, relate to a kind of preparation method and purposes in preparation treatment cardiovascular disease medicine thereof that derives from the total flavones of shepherd's purse medicinal material.
Background technology
According to the World Health Organization in October, 2008: cardiovascular disorder, transmissible disease and cancer are the current human three dead big major causes that cause, and the number of wherein dying from cardiovascular disorder is maximum, account for the whole world always death toll 29%.Analyze expectation according to world's heart alliance, the year two thousand twenty whole world cardiovascular death rate will increase by 50%, and its cardiovascular death number will wherein 1,900 ten thousand occur in developing country up to 2,500 ten thousand people.Cardiovascular disorder also is " the No.1 killer " of Chinese's health at present.China dies from nearly 3,000,000 (the accounting for crude death rate 45%) of cardiovascular disorder number every year, and the medical fee that is used for cardiovascular disorder is up to 1,300 hundred million yuan.Along with the raising of people's living standard, aging population and people's dietary structure changes, and activity reduces, and the intake of cholesterol and weight index are all increasing, and these all are the Hazard Factor that cause cardiovascular and cerebrovascular diseases.China recent years cardiovascular and cerebrovascular diseases sickness rate rises year by year, particularly at northern area.At present, China is in " window phase " of cardiovascular disorder outburst, must in time take effectively to intervene action, stops the fast development of cardiovascular diseases.Cardiovascular disorder is sick plant many, sickness rate is high, and human survival in close relations.Therefore prevention and treatment cardiovascular disorder are subjected to people's attention day by day, though it is more to treat the medicament categories of cardiovascular disorder in the market, the research that people capture cardiovascular disorder is still the task of top priority.
Shepherd's purse is the dry herb of Cruciferae (Cruciferae) plant shepherd's purse Capsella bursa-pastoris (L.) Medic..All there is distribution China various places, and Jiangsu, Anhui and suburb of Shanghai have cultivation, have that clearing heat and promoting diuresis, flat liver make eye bright, cooling blood for hemostasis and stomach disappear stagnant effect, and its main active ingredient is a flavones ingredient.The name beginning of shepherd's purse sees Tangsun and thinks in far away " a thousand pieces of gold food therapy ".All be called shepherd's purse before this.This product is used as medicine and is begun to see beam TAO Hong-Jing " Mingyi Bielu ", lists in top grade.Bright LI Shi-Zhen Compendium of Material Medica is released its day: " shepherd's purse is given birth to numerous, so the shepherd's purse of meaning "." shepherd's purse " of examining shepherd's purse be " together " together, and " together " person " Ji " also can cook to fill the stomach when this grass is hungry and prolong life, the life of can stopping blooding when hindering. effect is quite big, act on complete and so.The shepherd's purse in ancient times, kind is numerous and diverse.Song's TANG Shen-Wei " Classified Materia Medica " is drawn the words of beam code name doctor TAO Hong-Jing and is said " the shepherd's purse class is a lot of "; The Collective Notes to the Canon of Materia medica cloud: " the shepherd's purse class is many again, but this is the moderns trenchermans, and it is also good that leaf is made the marshland full of water weeds." poem " cloud: whose meaning tea hardship, it is sweet to be also as shepherd's purse.”
Once the seventies shepherd's purse was carried out chemical constitution study in eighties of last century abroad, find that its flavones ingredient that contains has violaguercitrin (rutin), Hesperidin (hesperidin) [Jurisson, S.Flavonoidsubstances of Capsella bursa-pastoris.Farmatsiya.1973,22 (5): 34-35], dihydrofisetin (dihydrofisetin), trifolitin-4-methyl ether (kaempferol-4-methylether), Quercetin-3-methyl ether (quercetin-3-methylether), gossypetin pregnancy ether (gossypetinhexamethyl ether), diosmin (diosmin), robinetin (robinetin), 3,4 ', 7-trihydroxy-flavanone (garbanzol) [Wohlfart Ranier, Gademann Rolf, Kirchner Carl Peter.Physiological-chemical observational changes in the flavonoid pattern ofCapsella bursa-pastoris.Deut.Apoth.-Ztg.1972,112 (30): 1158-1160], swertisin (swertisin) [Al-khalil Suleiman, Abu Zarga Musa, Zeitoun Nissreen, et al.Chemical constituents of Capsella bursa-pastoris.Alexandria J.Pharm.Sci.2000,14 (2): 91-94], luteolin-7-O-rutinoside (luteolin-7-O-galactoside), luteolin-7-O-galactoside (luteolin-7-O-rutinoside) [Nazmi Sabri N, Sarg T, Seif-El Din A.A.Phytochemical investigation of Capsella bursa-pastoris (L.) Medic.growing in Egypt.Egypt.J.Pharm.Sci.1975,16 (4): 521-522.].Domestic research to shepherd's purse is less, and The Chemical Constituents in the shepherd's purse is not arranged as yet, does not also see that total flavones in the shepherd's purse is used for the pertinent literature and the patent of cardiovascular disorder.In recent years, we carry out chemical constitution study to shepherd's purse, the multiple flavonoid compound of isolation identification, as tricin (tricin), trifolitin (kaempferol), Quercetin (quercetin), trifolitin-7-O-α-L-pyrans rhamnoside (kaempferol-7-O-α-L-rhamnopyranoside), Quercetin-3-O-β-D-glucopyranoside (quercetin-3-O-β-D-glucopyanoside), Lutonaretin (isoorientin), trifolitin-3-O-β-D-Glucopyranose-7-O-α-L-pyrans rhamnoside (kaempferol-3-O-β-D-glucopyanosyl-7-O-α-L-rhamnopyranoside), Quercetin-3-O-β-D-Glucopyranose-7-O-α-L-pyrans rhamnoside (quercetin-3-O-β-D-glucopyanosyl-7-O-α-L-rhamnopyranoside), trifolitin-3-O-rutinoside (kaempferol-3-O-rutinoside) [Ning Song, Wei Xu, Hongfeng Guan, XiaoqiuLiu, Yibo Wang, Xiaoling Nie.Several Flavonoids from Capsellabursa-pastoris.Asian Journal of Traditional Medicines, 2007,2 (5): 218-222] and 2 " O-α-L-arabinose Lutonaretin [Song Ning; Wang Rongrong; Li Zhanlin; Liu Xiaoqiu; Li Wen; Pei Yuehu .2D-NMR carries out structure elucidation to flavonoid glycoside in the shepherd's purse, the Wave Spectrum magazine, 2009,26 (1): 88-94.] etc.The invention provides the method for preparing shepherd's purse total flavones and high-purity monomer flavones and the purposes of total flavones aspect cardiovascular disorder of easy quick, cheap and suitable industrialized production.
Summary of the invention
One of purpose of the present invention is to provide a kind of total flavones of shepherd's purse and composition of one or more flavones of deriving from.
Two of purpose of the present invention is to provide the purposes of described shepherd's purse total flavones.
The total flavonoid of shepherd's purse provided by the invention extracts from the shepherd's purse medicinal material, and its content of total flavone is more than 60%, described high-purity monomer flavones comprises Lutonaretin and 2 " O-α-L-arabinose Lutonaretin.
Lutonaretin 2 " 0-α-L-arabinose Lutonaretin
The preparation method of shepherd's purse total flavones comprises the steps:
1) pre-treatment: the shepherd's purse medicinal material after will gathering dries the back segment, and is standby;
2) extract: 50～90% the extraction solvent that adds 5～12 times of amounts carries out refluxing extraction 1～4 time, and each extraction time is 0.5～3h, filters merging filtrate; Or add extraction solvent cold soak 12h～48h of 50～90% of 5～10 times of amounts, filter merging filtrate; Or add 50～90% the extraction solvent supersonic 0.5～3 hour of 5～15 times of amounts, filter merging filtrate.Described extraction solvent is methyl alcohol, ethanol or acetone.
3) concentrate: step 2) the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract.
4) upper prop: the medicinal extract that step 3) is obtained is to be splined on AB-8 or HPD-600 or D101 type macroporous resin, last sample flow velocity is 1～3BV/h, adopting the post blade diameter length ratio respectively is 1: 3～1: 7 macroporous adsorbent resin, last sample concentration is 0.3～0.5g/ml, and the concentration ethanol solution with 30%～90% carries out wash-out.
5) preparation: the elutriant collected is filtered, merging filtrate, concentrate drying obtains the extractive of general flavone of shepherd's purse.
Described step 2) extraction solvent is an ethanol, and it is 10 times of amounts that solvent is doubly measured, and extracting mode is a refluxing extraction, with 50% extraction using alcohol 3 times, extracts 1.5h at every turn.
The macroporous resin column of described step 4) is an AB-8 type macroporous resin, and last sample flow velocity is 3BV/h, and the post blade diameter length ratio is 1: 5, and alcohol concn is 50%.
Prepared content of total flavone is more than 60%.
Is AB-8 according to as above scheme with selecting macroporous resin in the step 4), and flow velocity is 3BV/h, and the post blade diameter length ratio is 1: 5, and last sample concentration is 0.5g/ml, and alcohol concn is 30%, 50%.The different ethanol elution parts that obtain are through polymeric amide chromatographic column or gel chromatographic columns or high performance liquid phase half preparative chromatography post, with the combination wash-out of trichloromethane or methylene dichloride or methyl alcohol or acetonitrile or water or the different ratios between them, " the O-α-two kinds of high purity flavones of L-arabinose Lutonaretin monomeric compound that obtains Lutonaretin and 2.
Be about to 50% ethanol elution that step 4) the obtains polyamide column chromatography of partly flowing through, use trichloromethane: methyl alcohol (20: 1) carries out wash-out, the wash-out part Sephadex LH-20 column chromatography of flowing through again, carry out wash-out with pure methyl alcohol, elutriant filters, merging filtrate, concentrate drying, obtain Lutonaretin, purity is more than 98%.30% ethanol elution that the obtains polyamide column chromatography of partly flowing through, use trichloromethane: methyl alcohol (20: 1) carries out wash-out, the wash-out part Sephadex LH-20 column chromatography of flowing through is again carried out wash-out with pure methyl alcohol, and pure methanol-eluted fractions is partly passed through high performance liquid phase semipreparative column chromatogram again, carry out wash-out with acetonitrile-water (15: 85), elutriant filters, merging filtrate, concentrate drying, " O-α-L-arabinose Lutonaretin, purity is more than 98% to obtain 2.
Simple, the easy row of extracting method provided by the invention, with the ultraviolet spectrophotometry is detection means, with 2 " O-α-L-arabinose Lutonaretin serves as to detect index; can carry out quality control to whole process flow; improved the content of flavone component effectively; the bulk drug purity height that obtains, and color and luster is good and have an anoxia functions that resists myocardial ischemia preferably; In addition, this extracting method uses conventional extraction equipment, and is cheap, easy to be quick, is suitable for suitability for industrialized production.
Embodiment
The preparation of embodiment 1, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 90% the alcohol reflux 3 times of 10 times of crude drug amounts, each extraction time is 1.5h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on HPD-600 type macroporous resin with 0.5g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 5, and the concentration ethanol solution with 70% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 61.9%.
The preparation of embodiment 2, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the methyl alcohol cold soaking that the shepherd's purse crude drug that obtains adds 8 times of crude drug amounts 60% extracts 12h, collect filtered liquid, filter, the filtrate concentrate drying that obtains obtains the extraction medicinal extract of shepherd's purse, the medicinal extract that obtains is splined on HPD-600 type macroporous resin with 0.4g/ml, last sample flow velocity is 2BV/h, and adopting the post blade diameter length ratio is 1: 5, and the concentration ethanol solution with 30% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 62.2%.
The preparation of embodiment 3, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds the methyl alcohol supersound extraction 0.5h of 5 times of crude drug amounts 50%, collect filtered liquid, filter, the filtrate concentrate drying that obtains obtains the extraction medicinal extract of shepherd's purse, the medicinal extract that obtains is splined on HPD-600 type macroporous resin with 0.3g/ml, last sample flow velocity is 1BV/h, and adopting the post blade diameter length ratio is 1: 7, and the concentration ethanol solution with 50% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 61.8%.
The preparation of embodiment 4, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the acetone cold soaking that the shepherd's purse crude drug that obtains adds 7 times of crude drug amounts 80% extracts 24h, collect filtered liquid, filter, the filtrate concentrate drying that obtains obtains the extraction medicinal extract of shepherd's purse, the medicinal extract that obtains is splined on AB-8 type macroporous resin with 0.3g/ml, last sample flow velocity is 2BV/h, and adopting the post blade diameter length ratio is 1: 5, and the concentration ethanol solution with 40% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 61.4%.
The preparation of embodiment 5, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds the ethanol ultrasonic extraction 1h of 10 times of crude drug amounts 70%, collect filtered liquid, filter, the filtrate concentrate drying that obtains obtains the extraction medicinal extract of shepherd's purse, the medicinal extract that obtains is splined on AB-8 type macroporous resin with 0.4g/ml, last sample flow velocity is 2BV/h, and adopting the post blade diameter length ratio is 1: 5, and the concentration ethanol solution with 60% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 60.2%.
The preparation of embodiment 6, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the ethanol cold soaking that the shepherd's purse crude drug that obtains adds 10 times of crude drug amounts 60% extracts 48h, collect filtered liquid, filter, the filtrate concentrate drying that obtains obtains the extraction medicinal extract of shepherd's purse, the medicinal extract that obtains is splined on D-101 type macroporous resin with 0.4g/ml, last sample flow velocity is 3BV/h, and adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 30% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 65.4%.
The preparation of embodiment 7, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds the acetone supersound extraction 3h of 15 times of crude drug amounts 90%, collect filtered liquid, filter, the filtrate concentrate drying that obtains obtains the extraction medicinal extract of shepherd's purse, the medicinal extract that obtains is splined on D-101 type macroporous resin with 0.5g/ml, last sample flow velocity is 2BV/h, and adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 70% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 63.2%.
The preparation of embodiment 8, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 80% the alcohol reflux 2 times of 8 times of crude drug amounts, each extraction time is 3h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on HPD-600 type macroporous resin with 0.4g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 80% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 60.2%.
The preparation of embodiment 9, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 70% the alcohol reflux 3 times of 12 times of crude drug amounts, each extraction time is 0.5h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on HPD-600 type macroporous resin with 0.4g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 70% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 61.8%.
The preparation of embodiment 10, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 70% the alcohol reflux 3 times of 10 times of crude drug amounts, each extraction time is 0.5h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on AB-8 type macroporous resin with 0.3g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 80% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 62.6%.
The preparation of embodiment 11, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 80% the alcohol reflux 2 times of 8 times of crude drug amounts, each extraction time is 1h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on AB-8 type macroporous resin with 0.4g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 90% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 60.8%.
The preparation of embodiment 12, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 70% the alcohol reflux 3 times of 10 times of crude drug amounts, each extraction time is 1.5h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on AB-8 type macroporous resin with 0.5g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 5, and the concentration ethanol solution with 50% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 63.6%.
The preparation of embodiment 13, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 90% the alcohol reflux 3 times of 10 times of crude drug amounts, each extraction time is 0.5h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on D-101 type macroporous resin with 0.3g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 80% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain the shepherd's purse total flavones.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 61.6%.
The preparation of embodiment 14, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 80% the alcohol reflux 2 times of 8 times of crude drug amounts, each extraction time is 1h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on D-101 type macroporous resin with 0.4g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 90% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain shepherd's purse total flavones thing.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 59.8%.
The preparation of embodiment 15, shepherd's purse total flavones
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 90% the alcohol reflux 3 times of 12 times of crude drug amounts, each extraction time is 0.5h, collects extracting solution, filters, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on D-101 type macroporous resin with 0.4g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 3, and the concentration ethanol solution with 90% carries out wash-out.Elutriant filters, merging filtrate, and concentrate drying, pulverizing obtain shepherd's purse total flavones thing.Shepherd's purse total flavones of the present invention, it is the yellowish brown powder, with 2, and " O-α-L-arabinose Lutonaretin is a reference substance, adopts spectrophotometry, measures optical density at 270nm, and calculating content of total flavone is 60.4%.
The preparation of Lutonaretin in embodiment 16, the shepherd's purse
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 70% the alcohol reflux 3 times of 10 times of crude drug amounts, each extraction time is 1.5h, collect extracting solution, filter, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on AB-8 type macroporous resin with 0.5g/ml, and last sample flow velocity is 3BV/h, adopting the post blade diameter length ratio is 1: 5, with 50% ethanol elution that the obtains polyamide column chromatography of partly flowing through, use trichloromethane: methyl alcohol (20: 1) carries out wash-out, again through Sephadex LH-20 column chromatography, carry out wash-out with pure methyl alcohol, elutriant filters, merging filtrate, concentrate drying, obtain Lutonaretin, purity is more than 98%.
2 " the preparations of O-α-L-arabinose Lutonaretin in embodiment 17, the shepherd's purse
Shepherd's purse medicinal material after gathering is dried the back segment, the shepherd's purse crude drug that obtains adds 70% the alcohol reflux 3 times of 10 times of crude drug amounts, each extraction time is 1.5h, collect extracting solution, filter, the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract, the medicinal extract that obtains is splined on AB-8 type macroporous resin with 0.5g/ml, last sample flow velocity is 3BV/h, and adopting the post blade diameter length ratio is 1: 5, with 30% ethanol elution that the obtains polyamide column chromatography of partly flowing through, use trichloromethane: methyl alcohol (20: 1) carries out wash-out, the wash-out part Sephadex LH-20 column chromatography of flowing through is again carried out wash-out with pure methyl alcohol, and pure methanol-eluted fractions is partly passed through high performance liquid phase semipreparative column chromatogram again, carry out wash-out with acetonitrile-water (15: 85), elutriant filters, merging filtrate, concentrate drying, " O-α-L-arabinose Lutonaretin, purity is more than 98% to obtain 2.
Embodiment 18,2, and " structure of O-α-L-arabinose Lutonaretin is identified
Yellow indefinite form powder, mp218～220 ℃, the Mg-HCl reacting positive, the Molish reacting positive, acid hydrolysis detects pectinose.Quasi-molecular ion peak m/z:619[M+K in the ESI-MS spectrum]
+, 581[M+H]
+, 579[M-H]
-
1H-NMR (600MHz, DMSO-d
6, δ) in the spectrum, 13.66 (1H, s, 5-OH), 7.41 (1H, dd, J=8.4,2.7Hz, H-6 '), 7.39 (1H, d, J=2.7Hz, H-2 '), 6.87 (1H, d, J=8.4Hz, H-5 '), 6.65 (1H, s, H-3), 6.44 (1H, s, H-8), 4.64 (1H, d, J=9.6Hz, H-1 "), 4.22 (1H; d, J=6.0Hz, H-1 " '), 4.29 (2H, m, H-2 "), 3.68 (1H, d, J=11.4Hz, H-6 "), 3.41 (1H, br.s, H-4 " '), 3.41 (1H, br.s; H-3 "), 3.29 (1H, br.s, H-4 "), 3.26 (1H; br.s, H-3 " '), 3.16 (1H, br.s, H-5 "); 3.16 (1H, br.s, H-2 " '), 3.02 (1H, m,, H-5 " '), 2.88 (1H, br.s, H-5 " ').
1C-NMR (150MHz, DMSO-d
6, δ) in the spectrum, 182.0 (C-4), 164.2 (C-7), 163.7 (C-2), 161.9 (C-9), 156.5 (C-5), 149.8 (C-4 '), 145.8 (C-3 '), (121.5 C-1 '), 119.0 (C-6 '), 116.2 (C-5 '), (113.4 C-2 '), 108.2 (C-6), 105.4 (C-1 " '); 103.4 (C-10), 102.8 (C-3), 93.0 (C-8); 81.8 (C-5 "), 80.4 (C-2 "), 78.8 (C-3 "), 72.5 (C-3 " '), 71.5 (C-4 "), 71.2 (C-1 "); 70.6 (C-2 " '), 67.0 (C-4 " '), 64.6 (C-5 " '), 61.5 (C-6 ").
Embodiment 19 shepherd's purse total flavoness are to the normal pressure hypoxia tolerance experiment of acute myocardial ischemia mouse due to the Racemic isoproterenol
Get 40 of healthy Kunming mouses, the male and female dual-purpose, body weight 20 ± 2g, be divided into four groups at random: normal control group, model control group, shepherd's purse total flavones group and metoprolol group, difference tail vein injection medicine, normal control group tail vein injection isometric(al) physiological saline, each administration group volume is 0.1ml/10g.After the administration after 5 minutes except that normal control group injection isometric(al) physiological saline, each organizes mouse peritoneal injection Racemic isoproterenol (Iso) 10mg/kg, each is organized the administration volume and is 0.2ml/10g, immediately mouse is put into the 250ml ground wide-necked bottle that fills the 15g sodica calx after 10 minutes, the Vaseline sealing.Be as the criterion each treated animal survival time of observed and recorded with last breathing.
The result: experimental data shows that compare with the normal control group, the model control group mouse survival time significantly reduces, and shepherd's purse total flavones (60mg/kg) group is compared mouse survival time significant prolongation with model control group.Prompting shepherd's purse total flavones has provide protection to the myocardial ischemia-anoxemia due to the Iso.The results are shown in Table 1.
Table 1 acute myocardial ischemia mouse normal pressure hypoxia tolerance experimental result
With normal control group ratio,
###P＜0.001; With the model control group ratio,
* *P＜0.001
Claims (7)
1, a kind of method of extracting high-purity monomer flavones and total flavones thereof from shepherd's purse, it is characterized in that: the content of this method gained total flavones material is more than 60%.
2, the preparation method of shepherd's purse high-purity monomer flavones as claimed in claim 1 and total flavones thereof, its feature may further comprise the steps:
1) pre-treatment: the shepherd's purse medicinal material after will gathering dries the back segment, and is standby;
2) extract: 50～90% the extraction solvent that adds 5～12 times of amounts carries out refluxing extraction 1～4 time, and each extraction time is 0.5～3h, filters merging filtrate; Or add extraction solvent cold soak 12h～48h of 50～90% of 5～10 times of amounts, filter merging filtrate; Or add 50～90% the extraction solvent supersonic 0.5～3 hour of 5～15 times of amounts, and filter, merging filtrate, described extraction solvent is methyl alcohol, ethanol or acetone.
3) concentrate: step 2) the filtrate concentrate drying that obtains, obtain shepherd's purse and extract medicinal extract.
4) upper prop: the medicinal extract that step 3) is obtained is to be splined on AB-8 or HPD-600 or D101 type macroporous resin, last sample flow velocity is 1～3BV/h, adopting the post blade diameter length ratio respectively is 1: 3～1: 7 macroporous adsorbent resin, last sample concentration is 0.3～0.5g/ml, and the concentration ethanol solution with 30%～90% carries out wash-out.
5) preparation: the elutriant collected is filtered, merging filtrate, concentrate drying obtains the extractive of general flavone of shepherd's purse.
6) purifying: the different ethanol elutions part that step 4) is obtained is through polymeric amide chromatographic column or gel chromatographic columns or high performance liquid phase half preparative chromatography post, with the combination wash-out of trichloromethane or methylene dichloride or methyl alcohol or acetonitrile or water or the different ratios between them, " the O-α-two kinds of high purity flavones of L-arabinose Lutonaretin monomeric compound that obtains Lutonaretin and 2.
3, the preparation method of shepherd's purse high-purity monomer flavones according to claim 2 and total flavones thereof, it is characterized in that described step 2) extracting mode is for refluxing, and the refluxing extraction method is with 50% extraction using alcohol 3 times, it is 10 times that solvent is doubly measured, and each extraction time is 1.5h.
4, according to claim 2 described shepherd's purse high-purity monomer flavones and total flavones thereof the preparation method, it is characterized in that: the macroporous resin column of described step 4) is an AB-8 type macroporous resin, and last sample concentration is 0.5g/ml, and flow velocity is 3BV/h, the post blade diameter length ratio is 1: 5, and alcohol concn is 30%, 50%.
5, the preparation method of shepherd's purse high-purity monomer flavones according to claim 2 and total flavones thereof, it is characterized in that: Lutonaretin is prepared as 50% ethanol elution that will the obtain polyamide column chromatography of partly flowing through in the described step 6), use trichloromethane: methyl alcohol (20: 1) carries out wash-out, the wash-out part Sephadex LH-20 column chromatography of flowing through is again carried out wash-out with pure methyl alcohol, and elutriant filters, merging filtrate, concentrate drying obtains Lutonaretin, and purity is more than 98%.
Lutonaretin
6, the preparation method of shepherd's purse high-purity monomer flavones according to claim 2 and total flavones thereof, it is characterized in that: in the described step 6) 2 " O-α-L-arabinose Lutonaretin be prepared as 30% ethanol elution that will the obtain polyamide column chromatography of partly flowing through; use trichloromethane: methyl alcohol (20: 1) carries out wash-out; the wash-out part Sephadex LH-20 column chromatography of flowing through again; carry out wash-out with pure methyl alcohol; pure methanol-eluted fractions is partly passed through high performance liquid phase semipreparative column chromatogram again; carry out wash-out with acetonitrile-water (15: 85), elutriant filters, merging filtrate, concentrate drying obtains 2, and " O-α-L-arabinose Lutonaretin, purity is more than 98%.
2 " O-α-L-arabinose Lutonaretin
7, shepherd's purse monomer flavones and the total flavones application in preparation treatment cardiovascular disease medicine.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103301167A (en) * | 2013-05-22 | 2013-09-18 | 黄权芳 | Application of babysbreath isoorientin for preparing medicines for treating alcoholic liver injury |
| CN108653366A (en) * | 2018-06-26 | 2018-10-16 | 西南民族大学 | A kind of method of enriching and purifying stone lattice dish general flavone |
| CN110679818A (en) * | 2019-10-31 | 2020-01-14 | 陕西师范大学 | Multifunctional shepherd's purse water extract solid beverage and preparation method thereof |
| CN112007066A (en) * | 2020-10-15 | 2020-12-01 | 沈阳药科大学 | Capsella bursa-pastoris extract and preparation method and application thereof |
| CN115524424A (en) * | 2022-10-18 | 2022-12-27 | 江阴天江药业有限公司 | Capsella bursa-pastoris sample quality control method |
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2009
- 2009-04-28 CN CN200910011323A patent/CN101538297A/en active Pending
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| NING S. 等: "Several flavonoids from Capsella bursa-pastoris（L.）Medic.", 《ASIAN JOURNAL OF TRADITIONAL MEDICINES》 * |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103301167A (en) * | 2013-05-22 | 2013-09-18 | 黄权芳 | Application of babysbreath isoorientin for preparing medicines for treating alcoholic liver injury |
| CN103301167B (en) * | 2013-05-22 | 2015-01-07 | 黄权芳 | Application of babysbreath isoorientin for preparing medicines for treating alcoholic liver injury |
| CN108653366A (en) * | 2018-06-26 | 2018-10-16 | 西南民族大学 | A kind of method of enriching and purifying stone lattice dish general flavone |
| CN110679818A (en) * | 2019-10-31 | 2020-01-14 | 陕西师范大学 | Multifunctional shepherd's purse water extract solid beverage and preparation method thereof |
| CN112007066A (en) * | 2020-10-15 | 2020-12-01 | 沈阳药科大学 | Capsella bursa-pastoris extract and preparation method and application thereof |
| CN112007066B (en) * | 2020-10-15 | 2022-04-12 | 沈阳药科大学 | Capsella bursa-pastoris extract and preparation method and application thereof |
| CN115524424A (en) * | 2022-10-18 | 2022-12-27 | 江阴天江药业有限公司 | Capsella bursa-pastoris sample quality control method |
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