CN113354697B - Method for separating and purifying pectolinarin and linarin - Google Patents
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Abstract
The invention discloses a method for separating and purifying pectolinarin and linarin, which comprises the steps of medicinal material cleaning, hot water extraction, flocculation and sedimentation, filtration, macroporous resin enrichment, elution, concentration, dynamic axial compression column chromatography purification, semi-preparative liquid chromatography separation and purification and the like. The method disclosed by the invention overcomes the defects of complicated extraction, separation and purification processes, large organic solvent consumption, high energy consumption and the like of the traditional solvent, adopts a macroporous resin enrichment series dynamic axial compression column chromatography technology, has the advantages of definite process directivity, simplicity in operation, compact process and reduction of pollution risk links by real-time detection and flow collection switching operation on the premise of not changing the characteristic components of a target product, can realize complete separation of pectolinarigenin and linarin by further adopting semi-preparative liquid chromatography, and is high in separation efficiency and high in product purity.
Description
Technical Field
The invention belongs to the technical field of separation and purification, and particularly relates to a method for separating and purifying pectolinarin and linarin.
Background
Herba seu radix Cirsii Japonici (also called Carex Dactylicapni, radix Raphani, etc.), and its base plant is herba seu radix Cirsii Japonici of Cirsium of Compositae Cirsium japonicumDC. The dried aerial parts of Japanese thistle herb are used as the medicine and collected in the Chinese pharmacopoeia part I (2020 edition). Circium japonicum is cool in nature, sweet and bitter in taste; it enters heart and liver meridians. The Japanese thistle herb is rich in flavonoid components, and pectolinarin, linarin, hesperidin, linaloflavin and the like are reported.
The pectolinarigenin and the linarin are flavonoid oxygen glycoside compounds, have good physiological activities of resisting inflammation, protecting liver, reducing blood sugar, resisting tumor and the like, and have great development and utilization values. Through previous researches of the applicant, the content of the pectolinarin, the linarin and the like in the circium japonicum is low (the content of the pectolinarin in the cirium japonicum is not lower than 0.2 percent according to the regulation of pharmacopoeia). However, the Japanese thistle herb is perennial herb, is wild in hillside, roadside and the like, is distributed in south and north provinces of China, has rich resources and low cost, is convenient to artificially cultivate, and is an excellent source of pectolinarin and linarin.
The inventor finds that the pectolinarigenin is connected with a molecule of glucose at the C-7 position of the A ring of a mother nucleus structure by an O-glycosidic bond, and is connected with a molecule of rhamnose at the 6' position by a 6' -1 ' O-glycosidic bond. Linarin is similar to linarin except that the C-5 position of the A ring is not substituted by methoxy. Since linarin and linarin are very similar in structure, it is difficult to separate them by conventional separation methods and means.
CN102477055A discloses a method for extracting and purifying linarin from circium japonicum, which is obtained by cold soaking and extracting with low-carbon alcohol, then extracting with petroleum ether, extracting with n-butanol, performing macroporous resin column chromatography, removing impurities with acid and alkali, and repeatedly recrystallizing. The extraction and separation process has the defects of long time consumption, high energy consumption, large organic solvent consumption, low extraction and separation efficiency, poor environmental compatibility and the like.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a method for separating and purifying linarin and linarin, which overcomes the defects of complicated extraction, separation and purification processes, large organic solvent consumption and high energy consumption of the traditional method, and improves the purification efficiency and purity of the linarin and linarin.
The invention is realized by the following technical scheme:
a method for separating and purifying pectolinarin and linarin comprises the following steps:
(1) heating and extracting herba seu radix Cirsii Japonici with pure water, coarse filtering to obtain crude extractive solution, and flocculating
Settling, taking the supernatant, and filtering to obtain clear supernatant;
(2) enriching the clear supernatant by macroporous resin, eluting, concentrating, and filtering with membrane to obtain membrane filtrate;
(3) Purifying the membrane filtrate by dynamic axial compression column chromatography, and collecting fluid containing pectolinarin and linarin by LC-qTOF-MS method for rapid identification of accurate molecular weight and locking retention time of reference substance to obtain herba seu radix Cirsii Japonici total glycosides;
(4) separating and purifying herba seu radix Cirsii Japonici total glycosides by semi-preparative liquid chromatography to obtain pectolinarin and linarin.
Preferably, in the step (1), the extraction time of the pure water is 1-4 hours, the extraction temperature is 90-95 ℃, the extraction times are 1-2 times, and the ratio of material to liquid is 1: 10-30.
Preferably, in the step (1), the rough filtration of the extracting solution is to filter the extracting solution by connecting a 90-100 mu m sintered metal filter head with a vacuum pump.
Preferably, in the step (1), the supernatant is filtered by connecting a 50-60 mu m sintered metal filter head with a vacuum pump.
Preferably, in the step (2), the macroporous resin is AB-8 or D-101, and the elution solvent is 70-95% methanol or ethanol.
Preferably, in step (3), the dynamic axial compression column is compressed by C18The reverse phase silica gel bonded phase is filler; methanol is taken as a mobile phase A and 0.05 percent formic acid aqueous solution is taken as a mobile phase B; gradient elution, wherein the elution procedure is 0-17 min, and 95% B → 44% B; 17-21 min, 44% B → 38% B; 21-32 min, 38% B → 5% B; 32-35 min, 5% B → 5% B; 35-37 min, 5% → 95% B; 37-45 min, 95% B → 95% B; flow rate 70 mL/min -1The detection wavelength is 254nm and 330 nm, the column temperature is 25 ℃, and the sample injection amount is 10 mL.
Preferably, in the step (4), the semi-preparative liquid chromatography conditions are as follows: octadecylsilane chemically bonded silica is used as a filler; using methanol and acetonitrile 1:1 as a mobile phase A and 0.05% formic acid aqueous solution as a mobile phase B, and performing gradient elution: 0-90 min, 95% B → 30% B; 90-92 min, 30% B → 5% B; 92-100 min, 5% B → 5% B; 100-102 min, 5% B → 95% B; 102-110 min, 95% B → 95% B; flow rate 4 mL/min-1The detection wavelengths are 254nm and 330 nm, the column temperature is 25 ℃, and the sample injection amount is 900 muL.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a novel method for separating and purifying pectolinarin and linarin, which overcomes the defects of complicated process, large organic solvent consumption and high energy consumption of the traditional extraction, separation and purification process, adopts a macroporous resin enrichment and series dynamic axial compression column chromatography technology, and reduces pollution risk links by real-time detection, flow fraction collection and switching operation, clear process directivity, simple and compact operation and the like on the premise of not changing characteristic components of a target product.
The invention further adopts semi-preparative liquid chromatography, can realize the complete separation of pectolinarin and linarin, and has high separation efficiency and high product purity. By adopting the method, the purity of the linarin and the pectolinarigenin can reach more than 95 percent.
Drawings
FIG. 1 is a chromatogram of pectolinarin and linarin prepared by the present invention;
FIG. 2 is a high-resolution mass spectrum of linarin (A) prepared by separation according to the present invention;
FIG. 3 is a high resolution mass spectrum of pectolinarin (B) separated and prepared by the present invention;
FIG. 4 is a chromatogram of pectolinarin and linarin prepared in comparative example 1;
FIG. 5 is a chromatogram of pectolinarin and linarin prepared in comparative example 2.
Detailed Description
The present invention is further illustrated by the following specific embodiments, which are not intended to limit the scope of the invention.
Example 1:
(1) taking 1kg of the overground part of Japanese thistle as a raw material, cleaning, removing impurities, adding pure water, heating and extracting for 2 times at 90-95 ℃, wherein the ratio of materials to liquids in the first extraction is 1: 20, the extraction time is 2 hours, and the ratio of the material to the liquid in the second extraction is 1: 15, the extraction time is 1.5h,
coarse filtering the two extracting solutions by connecting a 90-100 mu m sintered metal filter head with a vacuum pump, combining to obtain a coarse extracting solution, adding a flocculating agent (0.005% polyacrylamide) into the coarse extracting solution for flocculation and sedimentation, taking supernatant, and filtering the supernatant by connecting a 50-60 mu m sintered metal filter head with a vacuum pump to obtain clarified supernatant;
(2) Pouring the clear supernatant into pretreated D101 macroporous adsorption resin, and statically adsorbing for 12 hours; filtering out the resin after adsorption, rinsing with 2 times of pure water, eluting with 95% ethanol for 3 times, 30 minutes each time, collecting the eluent, dissolving with 70% ethanol after vacuum concentration, and filtering with a 0.45 mu m membrane;
(3) preparing a chromatographic system by adopting Jiangsu Hanbang science and technology Limited, configuring an NP7000 infusion pump and an NU3000 UV/VIS detector, connecting a DAC-HB dynamic axial compression column (50 multiplied by 650 mm) in series, taking octadecylsilane chemically bonded silica (C18, Hua Spectrum New science and technology Limited, ZK 2016080701) as a filler, taking methanol (A) and 0.05% formic acid aqueous solution (B) as mobile phases, and carrying out gradient elution, wherein the elution procedure is 0-17 min, and 95% B → 44% B; 17-21 min, 44% B → 38% B; 21-32 min, 38% B → 5% B; 5% B → 5% B; 35-37 min, 5% → 95% B; 37-45 min, 95% B → 95% B; flow rate 70 mL/min-1The detection wavelengths are 254nm and 330 nm, the column temperature is 25 ℃, and the sample injection amount is 10 mL. Collecting fluid containing pectolinarin and linarin by LC-qTOF-MS method for rapid identification of accurate molecular weight and locking retention time of reference substance to obtain herba seu radix Cirsii Japonici total glycosides.
(4) The method comprises the steps of adopting a semi-prepared chromatograph of Hanbang technology Limited, Jiangsu, configuring an NP7000 infusion pump and an NU3000 UV/VIS detector, preparing a liquid chromatographic column Phenomenonex Luna C18100A (250 x 10mm, 10 mu m) by using an octadecylsilane chemically bonded silica filler (C18) as a chromatographic column, and performing gradient elution (0-90 min, 95% B → 30% B, 90-92 min, 30% B → 5% B, 92-100 min, 5% B → 5% B, 100-102 min, 5% B → 95% B, 102-110 min, 95% B → 95% B) by using methanol, acetonitrile (1:1) (A) and 0.05% formic acid aqueous solution (B) as mobile phases-1The detection wavelength is 254nm and 330 nm, the column temperature is 25 ℃, and the sample injection amount is 900 mu L. Under the condition, the retention time of linarin and linarin is 70.968min and 72.132 min respectively, and baseline separation is basically achieved, and the chromatogram is shown in figure 1.
Collecting the above two compounds, vacuum concentrating, and freeze drying to obtain light yellow powder A (linarin) 0.042g and light yellow powder B (linarin) 0.502 g. Warp beam1H-and13C-NMR (Brookfield 500MHz Nuclear magnetic resonance spectrometer) analysisComparing with related literature data, and determining as linarin and linarin.
The invention separates the prepared pectolinarin 1H-NMR and13the C-NMR spectrum data are as follows:
1H-NMR (500 MHz, DMSO-d6) δ: 6.87 (1H, s, H-3), 6.83 (1H, brs,H-6), 7.02 (1H, brs, H-8), 7.99 (2H, d, J = 9.0 Hz,H-2′, 6′), 7.51 (2H, d, J = 9.0 Hz, H-3′, 5′), 3.70 (3H,s, -OCH3), 5.72 (1H, d, J = 7.5 Hz, Glc-H-1″), 4.10～4.70 (6H, m, Glc-H-2″～6″), 5.50 (1H, s, Rha-H-1"'),4.70～5.30 (6H, m, Rha-H-2"'′～5"'), 1.58 (3H, d, J =6.0 Hz, Rha-H-6"')；13C-NMR (150 MHz, DMSO-d6) δ:182.7(C-4), 164.5(C-2), 164.1(C-9), 163.1 (C-5),157.8(C-7), 106.6(C-10), 100.8(C-6), 95.3 (C-8),104.7(C-3), 162.5(C-4′), 128.7(C-2′,6′), 123.1(C-1′), 115.1 (C-3′,5′), 102.4(C-1″), 78.4 (C-5″), 77.7(C-3″), 74.7 (C-2″), 71.4 (C-4″), 67.6 (C-6″), 102.1(C-1"'), 74.1 (C-4"'), 72.8(C-3"'), 72.1 (C-2"'), 69.8(C-5"'), 18.6 (C-6"'), 55.5 (-OCH3)。
the method for separating and preparing the linarin1H-NMR and13the C-NMR spectrum data are as follows:
1H-NMR (500 MHz,DMSO-d6) δ: 8.03(d, J＝8.5 Hz, 2H, H-2', H-6'), 7.18(d,J＝8.6 Hz, 2H, H-3', H-5'), 6.94(s, 2H, H-3, H-8), 5.13 (d,J＝6.3 Hz, 1H, H-1"), 4.55(s, 1H, H-1"'), 3.85 (s, 3H, OMe), 3.76 (s, 3H, OMe), 3.69～3.60(m, 2H), 3.47 (dd, J＝10.2, 6.9 Hz, 2H),3.35～3.27 (m, 2H), 3.16 (dd, 2H),1.05 (d, 3H, H-6"'); 13C-NMR (150 MHz,DMSO-d6) δ: 182.2 (C-4), 163.9 (C-2), 162.2 (C-4'),159.4(C-7), 152.4(C-9), 152.1 (C-5), 132.5 (C-6),128.3 (C-2', C-6'), 122.5 (C-1'), 114.6 (C-3', C-5'),105.7 (C-10), 103.2 (C-3), 100.2 (C-1"'), 100.2(C-1"), 94.2 (C-8), 76.3 (C-3"), 75.6 (C-5"), 73.0(C-2"), 71.8 (C-4"'), 70.6 (C-3"'), 70.3 (C-2"'), 69.3(C-4"), 68.1 (C-5"'), 65.8 (C-6"), 60.1 (6-OMe), 55.4(4'-OMe), 17.6 (C-6"')。
taking the linarin obtained in the step (3) and the linarin each about 10mg, accurately weighing, dissolving with 70% ethanol, and metering to 10 mL. Liquid chromatography (Waters model 2695 HPLC, DAD detector) analysis, area normalization, wherein the purity of linarin and linarin is 95.2% and 98.7%, respectively.
Comparative example 1:
steps (1) to (3) are the same as in example 1 except that step (4):
(4) adopting a semi-preparative chromatograph of Jiangsu Hanbang science and technology Limited, configuring an NP7000 infusion pump and an NU3000 UV/VIS detector, using an octadecyl silane bonded silica gel filler (C18) as a chromatographic column, semi-preparative a liquid chromatographic column Phenomenonex Luna C18100A (250 x 10mm, 10 mu m), using methanol (A) -0.05% formic acid aqueous solution (B) as a mobile phase, and carrying out gradient elution (0-10 min, 5% B → 51% B; 10-20 min, 51% B → 57% B; 20-21 min, 57% B → 5% B); 21-25 min, 5% B → 5% B; flow rate 4.0 mL/min-1The detection wavelength is 254nm and 330 nm, the column temperature is 25 ℃, and the sample injection amount is 400 muL. Under the condition, the retention time of linarin and linarin is 18.510min and 19.060min respectively.
The chromatogram is shown in FIG. 4.
Collecting the above two compounds, vacuum concentrating, and freeze drying to obtain light yellow powder A (linarin) 0.096g and light yellow powder B (linarin) 0.399 g.
Taking the linarin and pectolinarin obtained in the step (4) to be about 10mg respectively, accurately weighing, dissolving with 70% ethanol, and metering to 10 mL. Liquid chromatography (Waters model 2695 HPLC, DAD detector) analysis, area normalization, was used to determine the purity of linarin and linarin as 62.06% and 90.32%, respectively.
Comparative example 2:
steps (1) to (3) are the same as in example 1 except that step (4):
(4) adopts a semi-preparative chromatograph of Jiangsu Hanbang science and technology Limited company, an NP7000 infusion pump and an NU3000 UV/VIS detector are arranged, and a chromatographic column adopts an octadecylsilane chemically bonded silica filler (C18) semi-preparative liquid chromatographic column Phenomenonex Luna C18100A (250 x 10 m)m, 10 mu m), and gradient elution is carried out by taking methanol (A) -0.05% formic acid water solution (B) as a mobile phase (0-120 min, 95% B → 30% B; 120-122 min, 30% B → 95% B; 122-130 min, 95% B → 95% B, flow rate 4 mL/min-1(ii) a The detection wavelength is 254nm and 330 nm, the column temperature is 25 ℃, and the sample injection amount is 400 mu L. Under the condition, the retention time of linarin and linarin is 91.748min and 92.992 min respectively.
The chromatogram is shown in FIG. 5.
Collecting the two compounds, vacuum concentrating, and freeze drying to obtain light yellow powder A (linarin) 0.087g and light yellow powder B (linarin) 0.412 g.
Taking the linarin obtained in the step (4) and linarin each about 10mg, accurately weighing, dissolving in 70% ethanol, and metering to 10 mL. Liquid chromatography (Waters model 2695 HPLC, DAD detector) analysis, area normalization, gave linarin and linarin purities of 77.36% and 94.27%, respectively.
As can be seen from the results of comparative example 1 and comparative example 2, the separation time of comparative example 1 is short, but the separation effect is poor, and the purity of the obtained target compound is low; the separation time of the comparative example 2 is long, the separation effect is improved, the product purity is improved, but the best effect is not achieved; by adopting the method of the embodiment 1 of the invention, the separation effect is best, the product purity is high (can reach more than 95 percent), and the separation time is intermediate.
Claims (5)
1. A method for separating and purifying pectolinarin and linarin is characterized by comprising the following steps:
(1) heating and extracting herba seu radix Cirsii Japonici with pure water, coarse filtering to obtain coarse extractive solution, flocculating and settling the coarse extractive solution, collecting supernatant, and filtering to obtain clear supernatant;
(2) Enriching the clear supernatant by macroporous resin, eluting, concentrating, and performing membrane filtration to obtain membrane filtrate;
(3) purifying the membrane filtrate by dynamic axial compression column chromatography, rapidly identifying with LC-qTOF-MS accurate molecular weight, and locking the retention time of reference substanceThe method comprises collecting fluid fractions containing pectolinarin and linarin to obtain herba seu radix Cirsii Japonici total glycosides; the dynamic axial compression column is provided with C18The reversed phase silica gel bonding phase is filler; methanol is taken as a mobile phase A and 0.05 percent formic acid aqueous solution is taken as a mobile phase B; gradient elution, wherein the elution procedure is 0-17 min, and 95% B → 44% B; 17-21 min, 44% B → 38% B; 21-32 min, 38% B → 5% B; 32-35 min, 5% B → 5% B; 35-37 min, 5% B → 95% B; 37-45 min, 95% B → 95% B; flow rate 70 mL/min-1The detection wavelengths are 254nm and 330 nm, the column temperature is 25 ℃, and the sample injection amount is 10 mL;
(4) separating and purifying herba seu radix Cirsii Japonici total glycosides by semi-preparative liquid chromatography to obtain pectolinarin and linarin; the semi-preparative liquid chromatography conditions were: octadecylsilane chemically bonded silica is used as a filler; taking methanol, acetonitrile 1:1 as a mobile phase A and 0.05% formic acid aqueous solution as a mobile phase B, and performing gradient elution for 0-90 min, wherein 95% B → 30% B; 90-92 min, 30% B → 5% B; 92-100 min, 5% B → 5% B; 100-102 min, 5% B → 95% B; 102-110 min, 95% B → 95% B; flow rate 4 mL/min -1The detection wavelengths are 254nm and 330 nm, the column temperature is 25 ℃, and the sample injection amount is 900 muL.
2. The method for separating and purifying linarin and linarin according to claim 1, wherein in the step (1), the extraction time of the pure water is 1-4 hours, the extraction temperature is 90-95 ℃, the extraction times are 1-2 times, and the ratio of materials to liquids is 1: 10-30.
3. The method for separating and purifying linarin and linarin according to claim 1, wherein in the step (1), the rough filtration of the extracting solution is performed by adopting a 90-100 mu m sintered metal filter head connected with a vacuum pump to filter the extracting solution.
4. The method for separating and purifying linarin and linarin according to claim 1, wherein in the step (1), the supernatant is filtered by adopting a sintered metal filter head connected with a vacuum pump and 50-60 mu m in a filtering manner.
5. The method for separating and purifying linarin and linarin as claimed in claim 1, wherein in step (2), the macroporous resin is AB-8 or D-101, and the elution solvent is 60-95% methanol or ethanol.
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| CN102250172A (en) * | 2011-07-13 | 2011-11-23 | 长沙华诚生物科技有限公司 | Method for extracting Buddleoside from wild chrysanthemum flowers |
| CN105403652A (en) * | 2016-01-06 | 2016-03-16 | 上海和黄药业有限公司 | Detection method of circium japonicum hemostasis slice fingerprint spectrum and application of detection method |
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| CN101955507A (en) * | 2010-05-26 | 2011-01-26 | 南京泽朗医药科技有限公司 | Method for preparing pectolinarin comparison product |
| CN102250172A (en) * | 2011-07-13 | 2011-11-23 | 长沙华诚生物科技有限公司 | Method for extracting Buddleoside from wild chrysanthemum flowers |
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