CN100409851C - Soy daidzin composition and preparation process and use thereof - Google Patents

Soy daidzin composition and preparation process and use thereof Download PDF

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CN100409851C
CN100409851C CNB031115357A CN03111535A CN100409851C CN 100409851 C CN100409851 C CN 100409851C CN B031115357 A CNB031115357 A CN B031115357A CN 03111535 A CN03111535 A CN 03111535A CN 100409851 C CN100409851 C CN 100409851C
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dry powder
compositions
composition
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游松
吕显刚
任杰
贾娴
赵晓丹
梁士民
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Shenyang Pharmaceutical University
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The present invention relates to compositions of soybean isoflavone glycoside, and a preparing method and the application thereof. The present invention provides 3 compositions of soybean isoflavone glycoside for preparing medicine for treating climacteric syndrome and obliterative cardiovascular and cerebrovascular diseases of persons in middle and old age caused by female hormone lack. The composition contains the compositions of isoflavone glycoside, such as soybean glycoside, glycitein glycoside and genistin. The composition contains 90% to 100% of 3 kinds of isoflavone glycoside; meanwhile, the composition contains 2 to 3 parts of isoflavone glycoside, 1 to 2 parts of glycitein glycoside and 3 to 4 parts of genistin. The composition can be prepared into various dosage forms. Soybeans are extracted with alcohol, and extracted liquid is concentrated, and is extracted by petroleum ether; extracted liquid is dried by vacuum to obtain dry powder; the dry powder is dissolved, and solution is made to pass through a macroporous adsorptive resin column to obtain eluate; the eluate is dried by vacuum to obtained dry powder; the sample stir of dry powder is carry out with silica gel; the chromatography of the dry powder is carried out with a silica gel column; eluate is concentrated, and is dried by vacuum to obtain the compositions.

Description

Soybean isoflavone aglycones composition and method of making the same and purposes
Technical field:
The present invention relates to medical technical field, exactly it is a kind of soybean isoflavone aglycones composition and method of making the same and purposes.
Background technology:
Soybean isoflavone aglycones is the isoflavone like substance that extracts in the Semen sojae atricolor.Semen sojae atricolor is the mature seed of legume soybean Glycinemax (L.) Merr., is one of China and world many countries and geographic main food variety.As a kind of functional food, Shennong's Herbal had been put down in writing Semen sojae atricolor and medical value thereof first in B.C. 2838, was listed as " middle product ".Isoflavonoid is present in the various plants body, is the class important substance that generally acknowledge in plant amedica extraction field, and Semen sojae atricolor is the valuable source of isoflavone especially.At present its research is mainly concentrated on the effect of isoflavone as phytohormone, think that its estrogen-like effects is because their structure and estrogen diethylstilbestrol structural similarity.Because the life-time service hormone improves the incidence rate of uterus carcinoma, is therefore just seeking alternative medicine.Secular clinical trial certificate: soybean isoflavone can replace estrogen and receptors bind performance estrogen-like effects, can disturb estrogen and receptors bind again, the effect of performance estrogen antagonist sample (AmJ Clin Nutr 1998Dec, 68 (6Suppl): 1500s.).Soybean isoflavone can be prevented and treated as climacteric syndrome, osteoporosis, blood fat rising etc. the horizontal person of low estrogen; For the horizontal person of high estrogen, can prevent and treat breast carcinoma, endometritis, have two-ways regulation equilibrium function (Public Health Nutr 1999Dec, 2 (4): 489).In addition, soybean isoflavone helps prophylaxis of tumours to be taken place, human body immunity improving function, antiinflammatory, cholesterol reducing, effect such as angiocardiopathy preventing generation (Nippon Rinsho 2000Dec, 58 (12): 2434).
Soybean isoflavone is the Polyphenols mixture, the composition of soybean isoflavone, existence form mainly comprise genistein (genistein) (J Am Chem Soc, 1941,63:3273), Daidezin (daidzein) (Phytochemistry, 1973,12:169) and Glycitein (glycitein) (Agric Biol Chem, 1979,43:1415).They exist with the beta-glucosidase form mostly under the native state.What wherein play physiological function mainly is genistin (Genistin), daiazi (Daidzin) and Glycitein glycosides (Glycitin).
Contain higher Daidezin and genistein in the bean product, account for 0.3%～1.4% of dry weight.As containing 2014ug/g in the Semen sojae atricolor powder, contain the 531ug/g dry weight in the bean curd, contain the 1918ug/g dry weight in the Semen sojae atricolor instant beverage.Derive from the Semen sojae atricolor of country variant, because growing environment, storage condition and time difference make Daidezin, genistein content that certain variation be arranged, generally the mean ratio of Daidezin and genistein, Glycitein be 1: 1: 0.2 (Pro Soc E Bio Med, 1998,217:263).At present, the product that market is relevant with soybean isoflavone all is meant based on soybean extract, its total isoflavone content is 10%, 20%, 40%, 60% not wait, and the product index content of each enterprise is indeterminate, also disunity, more do not have index components in proportions regulation, country does not have clearly unified standard yet.China Patent No.: 97120435 disclose the patent of invention that a kind of name by the application of U.S. Protein Technologies International, Inc is called " method that two steps of vegetable protein isoflavone conjugate is changed into Agl ", China Patent No.: 98805694 disclose the patent of invention that a kind of name by the application of U.S. Novogen INC. is called " preparing isoflavone from leguminous plant ", China Patent No.: 98807930 disclose the patent of invention that a kind of name by the application of a Japanese Pharmaceutical Co., Ltd is called " compositions of isoflavone-containing ", China Patent No.: 98119864 disclose the patent of invention that a kind of name is called " method of extracting isoflavone in the Semen sojae atricolor ", China Patent No.: 00120879 discloses the patent of invention that a kind of name is called " method of separation and refining soybean isoflavone from soybean meal ", China Patent No.: 00122917 discloses the patent of invention that a kind of name is called " extracting isoflavone simultaneously from de-fatted soybean dregs; Saponin; low sugar and the proteic method of getting ", and above-mentioned patent is seen with the present invention all inequality from the content and the process route of invention.
Summary of the invention:
The purpose of this invention is to provide a kind of soybean isoflavone aglycones composition and method of making the same and purposes, said composition contains three kinds of isoflavone aglycone chemical compounds: daiazi, Glycitein glycosides, genistin.Three kinds of isoflavone aglycones account for 90%～98.2% of compositions in the above-mentioned composition.Its preparation technology is as follows:
A) mixed solution of sophisticated full Semen sojae atricolor with ethanol or ethanol and water extracted, obtain extracting solution A.
B) extracting solution A concentrates after filtering, goes out ethanol, obtains concentrated solution B.
C) with concentrated solution B petroleum ether extraction, remove and deoil and lipophilic substance, water layer is concentrated vacuum drying, obtain dry powder C.
D) with dry powder C water dissolution, by macroporous adsorptive resins, reuse alcohol water elution obtains eluent D.
E) eluent D concentrates, and vacuum drying obtains dry powder E.
F) dry powder E is through silica gel mixed sample, alumina column chromatography, and the water-miscible organic solvent eluting, eluent concentrates, and vacuum drying obtains dry powder F.
G) dry powder F is through silica gel mixed sample, silica gel column chromatography, and the organic solvent eluting, eluent concentrates, and vacuum drying obtains the soybean isoflavone glycoside composition.
Said composition is fit to make various folk prescription pharmaceutical preparatioies.Described pharmaceutical preparation can be made into slow release or controlled-release pharmaceutical formulation.Pharmaceutical preparation can be made into coelenteron administration, spray delivery, ejection preparation, infusion preparation, Transdermal absorption or oral pharmaceutical preparation.Said composition can be used for preparing the medicine of treatment occlusive cardiovascular and cerebrovascular disease, as arteriosclerosis, coronary heart disease, cerebral thrombosis and hyperlipidemia.Above-mentioned composition also can be used for substituting soybean isoflavone and other medicines are formed compound medicinal formulation.
Three kinds of chemical compounds that obtain with preparation HPLC separation and purification, through UV, IR, 1H-NMR, 13C-NMR and MS spectroscopic identification structure are as follows:
Compound I is a white crystals, is dissolved in methanol, ethanol, is slightly soluble in chloroform, ether, and is water insoluble.
Ultraviolet absorption peak: λ MeOH261 and 322nm, maximum absorption band is at the 261nm place.MS shows [M] +Be 416. 13Show in the C-NMR spectrum (Fig. 1) and have 21 carbon signals.Remove 6 glucose carbon atom peaks of High-Field, 15 low carbon signals are arranged.Wherein (1H, low hydrogen signal s) can infer that thus this chemical compound is an isoflavonoid to the middle δ 8.38 of δ 174.8ppm carbonyl carbon signal, particularly the tertiary carbon signal δ 153.4ppm of low field and hydrogen spectrum (Fig. 2).By 3350cm in the IR spectrum (Fig. 3) -1Two hydroxyl peak, 1630cm -1Carbonyl peak, 1520 and 1470cm -1Locate strong skeletal vibration and confirmed further that also this chemical compound is an isoflavonoid.The structure of Compound I is:
Figure C0311153500061
Be daiazi (Daidzin), molecular formula is C 21H 20O 9
Compound I I is a white crystals, is dissolved in methanol, ethanol, is slightly soluble in chloroform, ether, and is water insoluble.
Ultraviolet absorption peak: λ MeOH262 and 331nm, maximum absorption band is at the 262nm place.MS shows [M] +Be 446. 13Show in the C-NMR spectrum (Fig. 4) and have 22 carbon signals.Remove 6 glucose carbon atom peaks of High-Field, 16 low carbon signals are arranged.δ 174.4ppm carbonyl carbon signal wherein, (1H, low hydrogen signal s) can infer that thus this chemical compound is an isoflavonoid to δ 8.37 in low tertiary carbon signal δ 151.6ppm and the hydrogen spectrum (Fig. 5).By 3400cm in the IR spectrum (Fig. 6) -1Two hydroxyl peak, 1630cm -1Carbonyl peak, 1520 and 1460cm -1Locate strong skeletal vibration and confirmed further that also this chemical compound is an isoflavonoid.The structure of Compound I I is:
Figure C0311153500062
Be Glycitein glycosides (Glycitin), molecular formula is C 22H 22O 10
Compound III is a white crystals, is dissolved in methanol, ethanol, is slightly soluble in chloroform, ether, and is water insoluble.
Ultraviolet absorption peak: λ MeOH253 and 300nm, maximum absorption band is at the 253nm place.MS shows [M] +Be 432. 13Show among the C-NMR (Fig. 7) and have 21 carbon signals.Remove 6 glucose carbon atom peaks of High-Field, 15 low carbon signals are arranged.No CH 3, CH 2, be tertiary carbon and quaternary carbon.Wherein (1H, low hydrogen signal s) can infer that thus this chemical compound is an isoflavonoid to the middle δ 8.43 of δ 180.54ppm carbonyl carbon signal, particularly the tertiary carbon signal δ 154.58ppm of low field and hydrogen spectrum (Fig. 8).By 3450cm in the IR spectrum (Fig. 9) -1And 3200cm -1Two hydroxyl peak, 1660cm -1Carbonyl peak, 1580 and 1500cm -1Locate strong skeletal vibration and confirmed further that also this chemical compound is an isoflavonoid.The structure of compound III is:
Figure C0311153500063
Be genistin (Genistin), molecular formula is C 21H 20O 10
So we obtain from soybean extract is that the pure product of three kinds of chemical compounds are three kinds of isoflavone aglycones, is respectively: daiazi, Glycitein glycosides, genistin.
It is that reference substance is drawn liquid phase working standard curve respectively as figure (10) that assay is made daiazi, Glycitein glycosides, genistin by oneself according to laboratory:
Described compositions detects (chromatographic column: ODS 4.6 * 250mm by HPLC; Wavelength: 260nm; Mobile phase: acetonitrile-water (20: 80) provides 3 peaks (Fig. 1), and peak 1 (7.9min) is daiazi (Daidzin), and peak 2 (8.4min) is Glycitein glycosides (Glycitin), and peak 3 (17.4min) is genistin (Genistin).
Contain three kinds of soybean isoflavone aglycones according to technical process markization of the present invention: the compositions of daiazi, Glycitein glycosides, genistin component, three's sum accounts for the 90%-98.2% of extract.Thereby for the standardization and the modernization of soybean isoflavone pharmaceutical preparation provides reliable material base.
The total content of daiazi, Glycitein glycosides, genistin is seen Figure 18 in the four batches of present compositions.
Advantage of the present invention is: the compositions of extracting from Semen sojae atricolor is provided, and said composition contains three kinds of isoflavone aglycone chemical compounds, has higher content in compositions.And a kind of comparatively simple and high-efficient extracting method is provided, can lack the medicine of diseases such as the climacteric syndrome, the sclerotin that cause are relaxed and comfortable and person in middle and old age's occlusive cardiovascular and cerebrovascular disease as the preparation treatment because of estrogen.Also can be used for substituting soybean isoflavone and other medicines composition compound medicinal formulation.
Description of drawings:
Fig. 1 is for Compound I among the present invention 13The C-NMR spectrogram.
Fig. 2 is for Compound I among the present invention 1The H-NMR spectrogram.
Fig. 3 is the IR spectrogram of Compound I among the present invention.
Fig. 4 is for Compound I I's among the present invention 13The C-NMR spectrogram.
Fig. 5 is for Compound I I's among the present invention 1The H-NMR spectrogram.
Fig. 6 is the IR spectrogram of Compound I I among the present invention.
Fig. 7 is for compound III among the present invention 13The C-NMR spectrogram.
Fig. 8 is for compound III among the present invention 1The H-NMR spectrogram.
Fig. 9 is the IR spectrogram of compound III among the present invention.
Figure 10 is that reference substance is drawn liquid phase working standard curve data table for three kinds of chemical compounds among the present invention.
Figure 11 is three kinds of isoflavone aglycone composition HPLC curve charts in the present composition.
Figure 12 is Compound I among the present invention 1H-NMR spectrum ownership table.
Figure 13 is Compound I among the present invention 13C-NMR spectrum ownership table.
Figure 14 is Compound I I among the present invention 1H-NMR spectrum ownership table.
Figure 15 is Compound I I among the present invention 13C-NMR spectrum ownership table.
Figure 16 is compound III among the present invention 1H-NMR spectrum ownership table.
Figure 17 is compound III among the present invention 13C-NMR spectrum ownership table.
Figure 18 is the total content table of daiazi, Glycitein glycosides, genistin in four batches of compositionss.
The specific embodiment:
Embodiment:
1. the full soybean-cake flour 1Kg of drying and ripening extracts 2 times with 60% ethanol water, and each 2 hours, concentrate behind the extracting liquid filtering, remove ethanol, obtain concentrated solution.The concentrated solution defat with petroleum ether concentrates water layer and vacuum drying once more, obtains dry powder 87g.With the dry powder water dissolution, by macroporous adsorptive resins, reuse alcohol water elution, after eluent concentrated, vacuum drying obtained dry powder 24g.Dry powder 24g carries out alumina column chromatography through mixing sample, chloroform methanol mixed solvent eluting, eluent concentrates, and vacuum drying obtains dry powder 15g, through silica gel mixed sample, silica gel column chromatography, chloroform methanol mixed solvent eluting, eluent concentrates, vacuum drying obtains the described compositions of this patent (hereinafter to be referred as this compositions) 9g.
2. this compositions 50g mixes with microcrystalline Cellulose 45g and magnesium stearate 5g, and mixture is used for beating sheet, every heavy 0.2g, and every contains this compositions 0.1g.In conjunction with symptom, obey the 1--2 sheet, every day 2--3 time at every turn.
3. this compositions 50g with corn starch 50g, adds water and makes soft material, crosses 12 mesh sieve pelletizes, and drying makes granule, incapsulates, and the heavy 0.2g of every capsules content contains this compositions 0.1g.In conjunction with symptom, obey the 1--2 sheet, every day 2--3 time at every turn.
4. this compositions 20g ploughs pure 20g with dextran-40 or mountain and phosphoric acid buffer mixes in right amount, is used for injection, uses water dissolution, by the general operation process of injection, makes every 5ml of injection, contains this compositions, 0.02g.In conjunction with symptom, prop up with 1--4 at every turn, mix use, every day 1 time with transfusions such as injecting sodium chloride.
5. this compositions 20g ploughs pure 20g with dextrose former times-40 or mountain and phosphoric acid buffer mixes in right amount, is used for injection, uses water dissolution, by the general operation process of injection, and fill, lyophilizing is made every of freeze dried injection and is contained this compositions 0.02g.In conjunction with symptom, prop up with 1--4 at every turn, mix use, every day 1 time with transfusions such as injecting sodium chloride.
Claim is not limited to institute and gives an actual example.Various oral formulations that said composition is made and injection can be used for treating diseases such as the climacteric syndrome, the sclerotin that cause because of the estrogen shortage are relaxed and comfortable, with the said composition is that the compound medicine of forming can be used for person in middle and old age's occlusive diseases of cardiovascular and cerebrovascular systems, as arteriosclerosis, coronary heart disease, cerebral thrombosis and hyperlipidemia.

Claims (5)

1. soybean isoflavone glycoside composition is characterized in that: extract the compositions of purification from legume soybean, contain three kinds of isoflavone aglycone chemical compounds in the said composition: daiazi (I), Glycitein glycosides (II), genistin (III), and structural formula is:
Three kinds of isoflavone aglycones account for 90%～98.2% of compositions, and its preparation technology is as follows:
A) mixed solution of sophisticated full Semen sojae atricolor with ethanol or ethanol and water extracted, obtain extracting solution A;
B) extracting solution A concentrates after filtering, removes ethanol, obtains concentrated solution B;
C) with concentrated solution B petroleum ether extraction, remove and deoil and lipophilic substance, water layer is concentrated vacuum drying, obtain dry powder C;
D) with dry powder C water dissolution, by macroporous adsorptive resins, reuse alcohol water elution obtains eluent D;
E) eluent D concentrates, and vacuum drying obtains dry powder E;
F) dry powder E is through silica gel mixed sample, alumina column chromatography, and the water-miscible organic solvent eluting, eluent concentrates, and vacuum drying obtains dry powder F;
G) dry powder F is through silica gel mixed sample, silica gel column chromatography, and the organic solvent eluting, eluent concentrates, and vacuum drying obtains the soybean isoflavone glycoside composition.
2. soybean isoflavone glycoside composition according to claim 1 is characterized in that: said composition is made various folk prescription pharmaceutical preparatioies.
3. soybean isoflavone glycoside composition according to claim 2 is characterized in that: said composition is made slow release or controlled-release pharmaceutical formulation.
4. according to claim 2 or 3 described soybean isoflavone glycoside compositions, it is characterized in that: said composition is made coelenteron administration, spray delivery, ejection preparation, Transdermal absorption or oral pharmaceutical preparation.
5. soybean isoflavone aglycones preparation of compositions method as claimed in claim 1 is characterized in that preparation technology is as follows:
A) mixed solution of sophisticated full Semen sojae atricolor with ethanol or ethanol and water extracted, obtain extracting solution A;
B) extracting solution A concentrates after filtering, removes ethanol, obtains concentrated solution B;
C) with concentrated solution B petroleum ether extraction, remove and deoil and lipophilic substance, water layer is concentrated vacuum drying, obtain dry powder C;
D) with dry powder C water dissolution, by macroporous adsorptive resins, reuse alcohol water elution obtains eluent D;
E) eluent D concentrates, and vacuum drying obtains dry powder E;
F) dry powder E is through silica gel mixed sample, alumina column chromatography, and the water-miscible organic solvent eluting, eluent concentrates, and vacuum drying obtains dry powder F;
G) dry powder F is through silica gel mixed sample, silica gel column chromatography, and the organic solvent eluting, eluent concentrates, and vacuum drying obtains the soybean isoflavone glycoside composition.
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CN100413497C (en) * 2004-04-14 2008-08-27 山东绿叶天然药物研究开发有限公司 Water soluble soybean aglycone medicinal composition and its preparing method
US7553505B2 (en) 2006-01-12 2009-06-30 The Hong Kong University Of Science And Technology Health care product containing isoflavone aglycones and method of producing the same
CN100410267C (en) * 2006-07-17 2008-08-13 北京宝泰宁堂生物技术有限公司 Soybean isoflavone extract, its preparation process and pharmaceutical compositions containing same
CN101716135B (en) * 2010-01-08 2012-11-14 山西医科大学 Soy isoflavone solid dispersion suppository and preparation method thereof
CN103121985A (en) * 2011-11-18 2013-05-29 邱国福 Beta-adrenergic blocking agent based on soy isoflavone derivatives and preparation method and purpose thereof
CN103145673B (en) * 2011-12-06 2015-05-20 安徽贝克生物制药有限公司 Daidzein derivative and pharmaceutically acceptable salt thereof
CN104546998B (en) * 2014-10-20 2017-09-29 长春大学 The production method of high genistin content isoflavones
CN105949257B (en) * 2016-06-08 2019-04-09 沈阳药科大学 A kind of preparation and use of isoflavone glycoside compound
CN110540557B (en) * 2019-06-17 2020-12-08 山东禹王生态食业有限公司 Method for preparing glycitein by taking soybean navel powder as raw material

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