CN104892702A - Method for extracting, separating and purifying two flavonoid glycosides from semen oroxyli - Google Patents
Method for extracting, separating and purifying two flavonoid glycosides from semen oroxyli Download PDFInfo
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- CN104892702A CN104892702A CN201510252991.7A CN201510252991A CN104892702A CN 104892702 A CN104892702 A CN 104892702A CN 201510252991 A CN201510252991 A CN 201510252991A CN 104892702 A CN104892702 A CN 104892702A
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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Abstract
The invention discloses a method for extracting, separating and purifying two flavonoid glycosides from semen oroxyli, and relates to the technical field of extraction, separation and purification of flavonoid glycosides from semen oroxyli. With the semen oroxyli medicinal material as a raw material, the method comprises the following steps: (1) extraction of the flavonoid glycosides in the semen oroxyli; (2) segregation analysis of the flavonoid glycosides in the semen oroxyli; (3) separation and purification of the flavonoid glycosides in the semen oroxyli; and (4) purity detection and structural identification of the compounds. Semipreparative high performance liquid chromatography is used for separation and purification, a mobile phase is methanol-water, and the two high-purity components are obtained and are authenticated to be baicalein-7-O-diglucoside and baicalein-7-O-glucoside respectively. The method has the advantages that baicalein-7-O-diglucoside and baicalein-7-O-glucoside are efficiently and fast extracted from the semen oroxyli, and the purities of the two compounds both reach 98% or more; and the technological process is green and environmentally friendly, no serious harm is generated to the environment, and the comprehensive cost is low.
Description
Technical field
The present invention relates to Semen Oroxyli extracting and developing purification of flavone glycosides technical field, specifically a kind of method of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli.
Background technology
Semen Oroxyli is the mature seed of Bignoniaceae plant oroxylum indicum Oroxylum indicum (L.) Vent., bitter, sweet, cool in nature, enters lung, liver, stomach warp, has the effect of removing heat from the lung and relieving sorethroat, cough-relieving, relax liver and stomach, pain relieving and heat-clearing.Be used for the treatment of clinically to cough into the upper respiratory tract infection of primary symptom, acute bronchitis, pharyngitis, pneumonia, Whooping cough and vocal cord disease.Pharmacological research shows, flavones is the main active ingredient of Semen Oroxyli, is also the leading indicator of Semen Oroxyli and related preparations quality control thereof.According to the literature, the method for separation and purification Semen Oroxyli kind flavonoid glycoside mainly contains repeatedly silica gel column chromatography and high-speed countercurrent chromatography, and the operating process of silica gel column chromatography is loaded down with trivial details, and the rate of recovery is lower, often uses the organic solvent that the toxicity such as chloroform, benzene is stronger; In high-speed countercurrent chromatography, the selection and comparison difficulty of solvent systems, lacks theoretical direction.Therefore, the method setting up flavonoid glycoside in a kind of efficient extracting and developing purifying Semen Oroxyli fast for in-depth Semen Oroxyli pharmacological research and improve quality control system etc. and have great importance.
Summary of the invention
The object of the present invention is to provide a kind of method of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli, efficient, quick, easy.
The present invention realizes with following technical scheme: a kind of method of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli, and concrete steps are as follows:
(1) extraction of flavonoid glycoside in Semen Oroxyli: by Semen Oroxyli pulverizing medicinal materials, extract with organic solvent, filter, extracting solution obtains crude extract through concentrating under reduced pressure, and the consumption of organic solvent is 6 ~ 20 times of Semen Oroxyli medicinal material consumption;
(2) compartment analysis of flavonoid glycoside in Semen Oroxyli: carry out compartment analysis with analysis mode high performance liquid chromatograph to the composition of crude extract in step (1), moving phase is the volume ratio 45:55 of methanol-water, methyl alcohol and water, and flow velocity is 1.0mL/min;
(3) separation and purification of flavonoid glycoside in Semen Oroxyli: carry out separation and purification with Semipreparative chromatography instrument to the composition in the crude extract obtained in step 1, moving phase is the volume ratio 50:50 of methanol-water, methyl alcohol and water, and flow velocity is 20 ~ 30mL/min; According to color atlas manual collection target components cut, concentrating under reduced pressure is except desolventizing;
(4) purity detecting of compound and Structural Identification: by after each target components cut concentrating under reduced pressure with dissolve with methanol, its purity high performance liquid chromatography detects, chromatographic condition is shown in step (2), the purity of 2 kinds of compounds all reaches more than 98%, is the two glucoside of scutellarin-7-O-and scutellarin-7-O-glucoside respectively through spectral analysis of the nuclear magnetic resonance 2 kinds of compounds.
It is further: the chromatographic column in step (2) analysis mode high performance liquid chromatograph adopts analysis mode C
18post, determined wavelength is 220nm, and column temperature is room temperature.
Chromatographic column in step (3) in Semipreparative chromatography instrument adopts semi-preparative C
18post, determined wavelength is 220nm, and column temperature is room temperature.
Step (1) extracting method is cold soaking, ultrasonic or reflux.。
Step (1) organic solvent is methyl alcohol or water or 50% ethanol or 70% ethanol or 95% ethanol.
Step (1) extraction time is 2-5 time; Extraction time is 1-3 hour.
Step (1) extraction time is 3 times; Extraction time is 2 hours.
Compartment analysis methanol-water eluent carries out wash-out in step (2), and type of elution is 40% methanol-water isocratic elution or 45% methanol-water isocratic elution or 50% methanol-water isocratic elution.
Step (3) separation and purification methanol-water eluent carries out wash-out, and type of elution has methanol-water gradient elution or 45% methanol-water isocratic elution or 50% methanol-water isocratic elution or 55% methanol-water isocratic elution.
The invention has the beneficial effects as follows: from Semen Oroxyli, extract the two glucoside of scutellarin-7-O-and scutellarin-7-O-glucoside efficiently, fast, the purity of 2 kinds of compounds all reaches more than 98%; Technological process environmental protection, to environment without serious harm, comprehensive cost is low.
Accompanying drawing explanation
Fig. 1 is the analysis mode high-efficient liquid phase chromatogram of Semen Oroxyli crude extract;
Fig. 2 is the Semipreparative chromatography figure of Semen Oroxyli crude extract;
Fig. 3 is high-efficient liquid phase chromatogram and the ultraviolet spectrogram of the two glucoside of scutellarin-7-O-;
Fig. 4 is high-efficient liquid phase chromatogram and the ultraviolet spectrogram of scutellarin-7-O-glucoside;
Embodiment
Describe technical scheme of the present invention in detail below in conjunction with embodiment and accompanying drawing, but protection domain is not by this restriction.In embodiment, equipment used or raw material all can obtain from market.Agents useful for same is all purchased from Tianjin chemical reagent three factory, and water used is deionized water.
From Semen Oroxyli, the method for extracting and developing purifying 2 kinds of flavonoid glycosides, the steps include:
(1) extraction of flavonoid glycoside in Semen Oroxyli: by Semen Oroxyli pulverizing medicinal materials, extract 3 times, each 2h with 15 times amount 70% alcohol heating reflux, filters, and merged by extracting solution, concentrating under reduced pressure obtains crude extract.
(2) compartment analysis of flavonoid glycoside in Semen Oroxyli: carry out compartment analysis with analysis mode high performance liquid chromatograph to the composition of crude extract, chromatographic column is analysis mode C
18post (250 × 4.6mm I.D., 5 μm), moving phase is methanol-water (45:55, V/V); Flow velocity is 1.0mL/min, and determined wavelength is 220nm, and column temperature is room temperature.
(3) separation and purification of flavonoid glycoside in Semen Oroxyli: carry out separation and purification with Semipreparative chromatography instrument to the composition in crude extract, chromatographic column is semi-preparative C
18post (250 × 25.4mm I.D., 10 μm), moving phase is methanol-water (50:50, V/V), and determined wavelength is 220nm, and column temperature is room temperature.According to color atlas manual collection target components cut, concentrating under reduced pressure is except desolventizing.
(4) purity detecting of compound and Structural Identification: by after each target components cut concentrating under reduced pressure with dissolve with methanol, its purity high performance liquid chromatography detects, chromatographic condition is shown in step (2), and analytical results shows that the purity of 2 kinds of compounds all reaches more than 98%.The two glucoside of scutellarin-7-O-and scutellarin-7-O-glucoside respectively through spectral analysis of the nuclear magnetic resonance 2 kinds of compounds.
Contriver makes moving phase by using the methyl alcohol of different concns, adopt different types of elution, the flow velocity controlling methanol-water eluent is 20-30mL/min (preferred 25mL/min), and optimized the purification condition realizing the object of the invention, regarding assay result is as follows:
The Semipreparative chromatography separation condition of table one Semen Oroxyli crude extract
| Elution requirement | |
| Embodiment 1 | 55% methanol-water isocratic elution |
| Embodiment 2 | 50% methanol-water isocratic elution |
| Embodiment 3 | 45% methanol-water isocratic elution |
| Embodiment 4 | Methanol-water gradient elution |
In embodiment 1, in elutriant, the concentration of methyl alcohol is higher, and elution time is shorter, and 2 kinds of separating effects between target compound and the impurity composition near it are all not ideal enough, and the purity of gained compound is lower.In embodiment 2, the moderate concentration of methyl alcohol in elutriant, be separated good between each composition, disengaging time is also comparatively suitable.In embodiment 3, in elutriant, the concentration of methyl alcohol is lower, and 2 kinds of separation case between target compound and the impurity composition near it are good, but disengaging time is oversize.Embodiment 4 adopts methanol-water gradient elution, also can obtain good separating effect within the suitable time, but causes being difficult to realize recycling because the concentration of elutriant constantly changes.
Fig. 1 is the analysis mode high-efficient liquid phase chromatogram of Semen Oroxyli crude extract.Fig. 2 is the Semipreparative chromatography figure of the Semen Oroxyli crude extract when selecting embodiment 2 system, and as seen from the figure, each component separating is good, and disengaging time is also comparatively suitable.According to color atlas manual collection each peak component, after recycling design, corresponding high-purity compound can be obtained.Through high performance liquid chromatography areas of peak normalization method analytical test, purity higher than 98%, this point can from Fig. 3 to Fig. 4 find out.In Fig. 1-4, I: scutellarin-7-O-two glucoside; II: scutellarin-7-O-glucoside.
Confirm that the chemical structural formula of 2 compounds that institute's extraction purification obtains is as follows through spectral analysis of the nuclear magnetic resonance:
The qualification result of 2 compounds is as follows:
The two glucoside of scutellarin-7-O-:
1h-NMR (400MHz, DMSO-d6): δ ppm:12.6 (1H, s, 5-OH), 8.6 (1H, s, 6-OH), 8.0 ~ 8.3 (2H, d, 2', 6'-H), 7.5 ~ 7.8 (3H, m, 3', 4', 5'-H), 7.2 (1H, s, 8-H), 7.1 (1H, s, 3-H), 5.1 (1H, d, J=6.4Hz, anomeric H of inner glucose), 4.2 (1H, d, J=6.3Hz, anomeric H of terminal glucose).
13c-NMR (100MHz, DMSO-d6): δ ppm:182.6 (C-5), 163.5 (C-2), 151.5 (C-9), 149.3 (C-7), 146.4 (C-6), 131.9 (C-4'), 130.8 (C-6or C-1'), 130.5 (C-1'or C-6), 129.1 (C-3', 5'), 126.4 (C-2'or C-6'), 106.1 (C-10), 104.6 (C-3), 104.5 (C-4), 103.7 (C-1 " '), 100.9 (C-1 "), 94.4 (C-8), 77.1 (C-5 " '), 76.8 (C-3 "), 75.7 (C-3 "), 75.6 (C-3 " '), 75.5 (C-2 " '), 73.2 (C-2 "), 70.2 (C-4 " or C-4 " '), 69.6 (C-4 " ' or C-4 "), 69.2 (C-6 "), 61.1 (C-6 " ').
Scutellarin-7-O-glucoside:
1h-NMR (400MHz, DMSO-d6): δ ppm:12.4 (1H, s, 5-OH), 8.4 (1H, s, 6-OH), 7.9 (2H, d, 2', 6'-H), 7.5 ~ 7.7 (3H, m, 3', 4', 5'-H), 7.1 (1H, s, 8-H), 7.0 (1H, s, 3-H), 5.1 (1H, d, J=6.4Hz, anomeric H).
13c-NMR (100MHz, DMSO-d6): δ ppm:182.9 (C-4), 163.9 (C-2), 151.9 (C-9), 149.7 (C-7), 146.8 (C-5), 132.5 (C-4'), 131.3 (C-6), 131.0 (C-1'), 129.6 (C-3', 5'), 126.8 (C-2', 6'), 106.5 (C-10), 105.2 (C-3), 101.3 (C-1 "), 94.7 (C-8), 77.8 (C-3 "), 76.3 (C-5 "); 73.5 (C-2 "), 70.0 (C-4 "), 60.9 (C-6 ").
The present invention is extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli, first extract by flavonoid glycoside constituents extraction out with 70% alcohol heating reflux; Following analysis mode high performance liquid chromatograph carries out compartment analysis to the composition of extract; Then, with Semipreparative chromatography instrument, separation and purification is carried out to the composition in extract and just can obtain 2 kinds of compounds; Finally, measure by the purity of high performance liquid chromatography to compound, identify according to the structure of spectral analysis of the nuclear magnetic resonance to compound.The method gained target compound purity is high, and foreign matter content is extremely low, this point can from Fig. 3 to Fig. 4 find out.In addition, also there is following advantage:
(1) carrying out extraction with 70% alcohol heating reflux to flavonoid glycoside composition in Semen Oroxyli is the principle that make use of " similar mix ", and the polarity of flavonoid glycoside is more weak, and the solubleness in 70% ethanol is maximum, and temperature raises, and solubleness increases.Therefore, extract with 70% alcohol heating reflux and can make flavonoid glycoside at utmost stripping, and oil-soluble impurities is not dissolved as far as possible.Not only increase extraction efficiency, and crude extract can be made pure as far as possible, reduce preparative C to greatest extent
18the contaminated degree of post.
(2) by high performance liquid chromatography, compartment analysis is carried out to the composition of Semen Oroxyli crude extract, make moving phase isocratic elution with methanol-water and can realize baseline separation to 2 kinds of target compounds at short notice.
(3) carry out separation and purification by Semipreparative chromatography method to compound, can obtain 2 kinds of high-purity monomer compounds, method is simple to operate, and efficiency is high, and process cycle is short, saves reagent, reduces production cost.
(4) measure the purity preparing gained compound by high performance liquid chromatography, the method accurately, fast.
(5) ethanol, first alcohol and water is only used in extracting and developing, purge process, do not use environment and the large organic solvent such as chloroform, benzene of harm, alcohol-water extracting solution and methanol-water eluent all can be reused repeatedly after underpressure distillation is reclaimed, environmental protection.
(6) optimize the condition (composition of elutriant and flow velocity) of chromatography method, the purity of compound and purification efficiency are all greatly improved.
Embodiment is the more representational example of the present invention, and obvious technical scheme of the present invention is not limited to above-described embodiment.A lot of distortion can also be had.Those of ordinary skill in the art, mentions or associates disclosed in from then in file, all should think the claimed scope of this patent.
Claims (9)
1. the method for extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli, is characterized in that: concrete steps are as follows:
(1) extraction of flavonoid glycoside in Semen Oroxyli: by Semen Oroxyli pulverizing medicinal materials, extract with organic solvent, filter, extracting solution obtains crude extract through concentrating under reduced pressure, and the consumption of organic solvent is 6 ~ 20 times of Semen Oroxyli medicinal material consumption;
(2) compartment analysis of flavonoid glycoside in Semen Oroxyli: carry out compartment analysis with analysis mode high performance liquid chromatograph to the composition of crude extract in step (1), moving phase is the volume ratio 45:55 of methanol-water, methyl alcohol and water, and flow velocity is 1.0mL/min;
(3) separation and purification of flavonoid glycoside in Semen Oroxyli: carry out separation and purification with Semipreparative chromatography instrument to the composition in the crude extract obtained in step 1, moving phase is the volume ratio 50:50 of methanol-water, methyl alcohol and water, and flow velocity is 20 ~ 30mL/min; According to color atlas manual collection target components cut, concentrating under reduced pressure is except desolventizing;
(4) purity detecting of compound and Structural Identification: by after each target components cut concentrating under reduced pressure with dissolve with methanol, its purity high performance liquid chromatography detects, chromatographic condition is shown in step (2), the purity of 2 kinds of compounds all reaches more than 98%, is the two glucoside of scutellarin-7-O-and scutellarin-7-O-glucoside respectively through spectral analysis of the nuclear magnetic resonance 2 kinds of compounds.
2. the method for a kind of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli according to claim 1, is characterized in that: the chromatographic column in step (2) analysis mode high performance liquid chromatograph adopts analysis mode C
18post, determined wavelength is 220nm, and column temperature is room temperature.
3. the method for a kind of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli according to claim 1, is characterized in that: the chromatographic column in step (3) in Semipreparative chromatography instrument adopts semi-preparative C
18post, determined wavelength is 220nm, and column temperature is room temperature.
4. the method for a kind of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli according to claim 1, is characterized in that: step (1) extracting method is cold soaking, ultrasonic or reflux.
5. the method for a kind of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli according to claim 1, is characterized in that: step (1) organic solvent is methyl alcohol or water or 50% ethanol or 70% ethanol or 95% ethanol.
6. the method for a kind of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli according to claim 1, is characterized in that: step (1) extraction time is 2-5 time; Extraction time is 1-3 hour.
7. the method for a kind of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli according to claim 5, is characterized in that: step (1) extraction time is 3 times; Extraction time is 2 hours.
8. the method for a kind of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli according to claim 1, it is characterized in that: step (2) compartment analysis methanol-water eluent carries out wash-out, type of elution is 40% methanol-water isocratic elution or 45% methanol-water isocratic elution or 50% methanol-water isocratic elution.
9. the method for a kind of extracting and developing purifying 2 kinds of flavonoid glycosides from Semen Oroxyli according to claim 1, it is characterized in that: step (3) separation and purification methanol-water eluent carries out wash-out, type of elution has methanol-water gradient elution or 45% methanol-water isocratic elution or 50% methanol-water isocratic elution or 55% methanol-water isocratic elution.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104876900A (en) * | 2015-05-18 | 2015-09-02 | 徐州医学院 | Method for extracting, separating and purifying costunolide and dehydrocostus lactone from elecampane |
| CN115232224A (en) * | 2022-08-04 | 2022-10-25 | 北京中医药大学 | Oroxylum indicum polysaccharide and medical application thereof in preparing medicine for treating ulcerative colitis |
-
2015
- 2015-05-18 CN CN201510252991.7A patent/CN104892702A/en active Pending
Non-Patent Citations (2)
| Title |
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| 张昌壮: "《HPLC法测定木蝴蝶中木蝴蝶苷A和木蝴蝶苷B的质量分数》", 《吉林大学学报》 * |
| 袁媛: "《高速逆流色谱在分离纯化木蝴蝶活性成分中的线性放大》", 《色谱》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104876900A (en) * | 2015-05-18 | 2015-09-02 | 徐州医学院 | Method for extracting, separating and purifying costunolide and dehydrocostus lactone from elecampane |
| CN115232224A (en) * | 2022-08-04 | 2022-10-25 | 北京中医药大学 | Oroxylum indicum polysaccharide and medical application thereof in preparing medicine for treating ulcerative colitis |
| CN115232224B (en) * | 2022-08-04 | 2023-06-30 | 北京中医药大学 | Oroxyli polysaccharide and medical application thereof in preparation of medicines for treating ulcerative colitis |
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