CN114573446B - Method for preparing protocatechuic acid from phellinus linteus medicinal material - Google Patents
Method for preparing protocatechuic acid from phellinus linteus medicinal material Download PDFInfo
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- CN114573446B CN114573446B CN202011403414.0A CN202011403414A CN114573446B CN 114573446 B CN114573446 B CN 114573446B CN 202011403414 A CN202011403414 A CN 202011403414A CN 114573446 B CN114573446 B CN 114573446B
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- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention provides a method for preparing protocatechuic acid from phellinus linteus medicinal material, which comprises the steps of extracting the phellinus linteus medicinal material with pure water, adopting a two-dimensional orthogonal liquid chromatography technology, enriching pure water resistant C8YE silica gel filler as a separation material to obtain crude protocatechuic acid in one dimension, and preparing and purifying the crude protocatechuic acid in two dimensions by using polar copolymerization C18HC bonded silica gel filler to obtain a protocatechuic acid product with the purity of more than 95 percent. The preparation process of the invention has stable process, high yield, high automation degree and easy operation, and can meet the requirement of large-scale production.
Description
Technical Field
The method relates to the technical field of separation and purification, in particular to a method for preparing protocatechuic acid from phellinus linteus medicinal materials. Furthermore, the invention relates to a method for preparing high-purity protocatechuic acid from phellinus linteus by utilizing a two-dimensional liquid chromatography technology, and the purity can reach more than 95%.
Background
Phellinus linteus is a precious perennial large-scale medicinal fungus, known as "forest gold", and recorded in Ben Cao gang mu. Forty species are distributed in China belonging to the genus Phellinus of family Polyporaceae, order Aphyllophorales, class Basidiomycotina. Mainly parasitizes on trunks of mulberry, willow, birch Yang Li and the like, wherein wild mulberry, mulberry Huang Zuiwei is used for the precious purpose.
Phellinus linteus is used as a traditional fungus traditional Chinese medicine in China, and is a first medical fungus with effective rate in the field of biological cancer treatment internationally recognized at present. It contains chemical components of various structural types, including polysaccharides, flavones, triterpenes, aromatic acids, amino acids, etc.; modern pharmacological experiments also show that Sang Huangju has various pharmacological activities such as anticancer, immunoregulation, anti-obesity, antioxidation, anti-inflammatory and the like.
In recent years, the search for a dual-target drug that has a neurotrophic-like effect and can enhance the effect of neurotrophic factors in natural compounds has become a hotspot of research. The research shows that protocatechuic acid has various effects of resisting cancer, resisting oxidation, resisting inflammation, reducing blood sugar and the like, and is a healthy and safe beneficial micromolecule substance.
Protocatechuic acid (3, 4-dihydroxybenzoic acid) is white powder, and has the following structural formula:
the protocatechuic acid has a plurality of-OH in molecular formula and has certain combination effect with silanol groups on the surface of silica gel, which is a main reason for serious tailing and difficult separation in the preparation process of the substance, and in order to solve the problem, the one-dimensional and two-dimensional separation filler used in the patent respectively adopts the technologies of multipoint mild bonding, tail sealing technology, polar copolymerization and the like to treat the surface of the filler, thereby greatly improving the tailing problem in the preparation process;
protocatechuic acid has various pharmacological activities of resisting platelet aggregation, reducing myocardial oxygen consumption, inhibiting bacteria, relieving pain, etc., and is an important natural active substance. Recent researches find that the compound has a plurality of novel pharmacological actions such as antioxidation, anticancer, mediated tumor cell apoptosis and the like; has certain nerve cell protecting effect on ischemic and anoxic neurons; can remarkably relieve inflammatory response of interleukin 1 beta to chondrocytes; can maintain the phenotype and proliferation promoting effect of damaged chondrocytes; maintaining chondrocyte phenotype and promoting cell proliferation, and the like.
Protocatechuic acid has strong antioxidant ability, has obvious inhibiting effect on Staphylococcus aureus, streptococcus, etc., and has effects of astringing and promoting wound healing, and can be used for treating inflammation, fever, cancer, etc.
The method for extracting and preparing protocatechuic acid from the phellinus linteus medicinal material has few reports and undefined spectrum effect relationship, so that the preparation of the compound has important significance for basic research and pharmacological activity research of phellinus linteus substances;
the invention is proposed in view of the above technical background and development prospect.
Disclosure of Invention
The invention provides a method for preparing protocatechuic acid by taking a phellinus linteus medicinal material as a raw material and adopting two-dimensional liquid chromatography, which comprises the following operation steps:
1. preferably, pure water extraction is adopted for Phellinus linteus medicinal materials, the ratio of feed to liquid is 1:15-30, soaking is carried out for 10-24 hours, boiling water is heated and boiled for 1-2 hours, extraction is carried out for 2-3 times, and water extract is obtained by combining;
2. preferably, the water extract is subjected to hollow fiber membrane filtration by adopting a membrane filtration technology, and the hollow fiber membrane filter core has the accuracy of 10000-800000 molecular weight, so as to obtain a hollow fiber membrane permeate;
3. preferably, pure water resistant C8YE silica gel filler is used, has good enrichment effect on protocatechuic acid, can directly load sample and enrich the hollow fiber membrane water phase permeate liquid in large volume, and has the particle diameter of 30-60 mu m and the pore diameter of
And enriching to obtain crude protocatechuic acid.
4. In order to realize the purpose of one-dimensional preparation of the crude product of the enriched protocatechuic acid, the invention adopts the following technical scheme:
the elution condition adopted in the one-dimensional liquid chromatography preparation is that acetone, acetonitrile and isopropanol (organic phase) are mixed with acid water (aqueous phase), the aqueous phase is one or two of acetic acid and phosphoric acid, the proportion is 0.1-0.5% (v/v), according to the isocratic of the organic phase, the linear gradient or the step gradient of 5-25%, the flow rate is 0.1-0.2 times of the filler volume/min, the temperature is 25-45 ℃, the sample loading amount is 0.5-3.0% (the ratio of the solid mass of a sample solution to the filler mass), the detector is a DAD ultraviolet detector, the elution time is 20-60 min, fractions are collected according to the chromatographic peak curve of the detector, liquid phase analysis is carried out on all the fractions, the protocatechuic acid fractions are confirmed, and after the protocatechuic acid fractions are combined, the protocatechuic acid crude product is prepared in one dimension by concentrating to 20-80 mg/mL;
5. preferably, the two-dimensional preparation adopts polar copolymerized C18HC bonded silica gel filler with the particle diameter of 10-40 mu m and the pore diameter of
Preparation to obtain purity>95% protocatechuic acid;
6. in order to achieve the purpose of preparing protocatechuic acid in two dimensions, the invention adopts the following technical scheme:
the two-dimensional liquid chromatography is prepared by mixing acetone, acetonitrile and isopropanol (organic phase) with formic acid water (aqueous phase), wherein the organic phase is 5-25% isocratic, the gradient or step isocratic is 5-25%, the aqueous phase is formic acid with the proportion of 0.1-1.2% (v/v), the flow rate is 0.2-0.3 times of filler volume/min, the temperature is 25-45 ℃, the sample loading amount is 0.2-2.0% (the ratio of sample mass to filler mass), the detector is a DAD ultraviolet detector, the elution time is 30-80 min, the components of protocatechuic acid are collected according to the chromatographic peak curve of the detector, and the obtained fraction is vacuum dried, so that protocatechuic acid with the purity of more than 95% can be obtained.
The invention has the following advantages:
compared with the prior art, the invention has the following characteristics:
1. the one-dimensional separation filler of the Phellinus linteus compound adopts a pure water resistant synthesis process, can carry out large-volume sample loading on a pure water phase sample, can avoid the problem that the bonding phase of the common C18 bonding filler is curled and loses retention, and the two-dimensional separation filler adopts a polar copolymerization C18HC bonding silica gel filler to carry out orthorhombic separation on the one-dimensional Sang Huanghua compound protocatechuic acid and has complementarity with the one-dimensional separation filler;
2. the purity of protocatechuic acid is high: the technical method directly aims at the protocatechuic acid contained in the medicinal material to prepare the protocatechuic acid without heating and changing acid base, and the protocatechuic acid is prepared in the state of existing in the medicinal material without hydrolysate doping, so that the purity of the obtained protocatechuic acid is high and reaches more than 95 percent.
3. The method for preparing protocatechuic acid has the advantages of high instrument automation degree, simple and convenient operation and high yield, and can meet the requirement of mass production.
Drawings
FIG. 1 is a one-dimensional preparation spectrum of protocatechuic acid of example 1;
FIG. 2 is a two-dimensional preparation spectrum of protocatechuic acid of example 1;
FIG. 3 is a liquid phase analysis chart of protocatechuic acid of example 1.
Detailed Description
The invention will now be further described with reference to examples. It should be noted that it will be apparent to those skilled in the art that several improvements and modifications can be made without departing from the technical principle of the present invention, and these improvements and modifications should also be considered as the scope of the present invention. The examples are only to illustrate the present invention, and the present invention is not limited thereto.
Example 1
Weighing Huang Yaocai g of mulberry, adding 3L of aqueous solution, soaking for 24 hours, heating and boiling for 8 hours, collecting aqueous extract, repeatedly adding 3L of aqueous solution into solid materials, boiling and collecting aqueous extract, repeatedly extracting for 1 time, combining to obtain aqueous extract of the phellinus linteus medicinal material, and filtering with a hollow fiber membrane (membrane core precision 100000 molecular weight).
One-dimensional preparation conditions, chromatographic conditions using C8YE packing (preparation column size: 100X 250mm, particle size 30 μm, pore size)
The mass is 1200g, the Hua spectrum is a new technology Co., ltd.), the mobile phase adopts (A) acetonitrile (organic phase) - (B) 0.1% acetic acid water (water phase, v/v), the gradient elution mode: eluting with pure water for 10min, increasing the volume concentration of acetonitrile (mobile phase A) from 10% to 20% by 60min (mobile phase B) for 60min, selecting 254nm absorption wavelength by DAD ultraviolet detector, preparing at 25deg.C, loading sample volume of 3.3L/needle, loading sample of 0.5% (ratio of solid mass of sample solution to filler mass), flowing at 300mL/min, collecting fractions according to detector chromatographic peak curve, subjecting all fractions to liquid phase analysis, confirming protocatechuic acid fraction, mixing, concentrating to 30mg/mL, and obtaining crude product of protocatechuic acid with one-dimensional preparation, purity of 36.51%, and yield of 86.9%.
Two-dimensional preparation conditions, chromatographic conditions using reversed phase C18HC bonded silica gel packing (preparation column specification: 50×150mm, particle size 10 μm, pore diameter)
300g mass, wanshi Spectrometry Ind Co., ltd.) and (A) acetone (organic phase) - (B) with 0.1% formic acid water (aqueous phase, mass concentration), isocratic eluting with 10% acetone (mobile phase (A) and (mobile phase (rest)) with DAD violetThe external detector selects 320nm absorption wavelength, the preparation temperature is 25 ℃, the sample injection amount is 20 mL/needle, the flow rate of the mobile phase is 60mL/min, the fraction of the protocatechuic acid is collected according to the chromatographic peak curve of the detector (collected according to chromatographic peaks), the protocatechuic acid is obtained by rotary evaporation to dryness (the product is determined to be the protocatechuic acid through nuclear magnetism and high resolution mass spectrum structural analysis), and the purity is 95.55 percent and the yield is 93.2 percent through liquid chromatography analysis.
Example 2
Weighing Huang Yaocai g of mulberry, dissolving in 2L of aqueous solution, soaking for 30 hours, heating, boiling for extraction for 6 hours, collecting aqueous extract, repeatedly adding 2L of aqueous solution into solid materials, boiling for extraction, collecting aqueous extract, repeatedly extracting for 2 times, combining to obtain aqueous extract of the phellinus linteus, obtaining aqueous extract of the phellinus linteus, filtering by using a hollow fiber membrane with membrane core precision of 500000 molecular weight, and concentrating permeate to 40mg/mL.
One-dimensional preparation conditions, chromatographic conditions using C8YE packing (preparation column size: 100X 250mm, particle size 60 μm, pore size)
The mass is 1200g, the Hua spectrum is a new technology Co., ltd.), the mobile phase adopts (A) acetonitrile (organic phase) - (B) 0.1% phosphoric acid water (water phase, v/v), the step isocratic elution mode: pure water is used for eluting for 20min, acetonitrile (mobile phase A) is used for isocratic eluting with the volume concentration of 20 percent (the balance is mobile phase B) for 60min, a DAD ultraviolet detector is used for selecting 254nm absorption wavelength, the preparation temperature is 25 ℃, the sample injection amount is 300 mL/needle, the sample loading amount is 0.75 percent (the ratio of the solid mass of a sample solution to the mass of a filler), the flow rate of the mobile phase is 300mL/min, fractions are collected according to a chromatographic peak curve of a detector, liquid phase analysis is carried out on all the fractions, protocatechuic acid fractions are confirmed, and are concentrated to 40mg/mL after being combined, so that a crude product of one-dimensional protocatechuic acid is obtained, the purity is 46.82 percent, and the yield is 90.1 percent.
Two-dimensional preparation conditions, chromatographic conditions using reversed phase C18HC bonded silica gel packing (preparation column specification: 50×150mm, particle size 10 μm, pore diameter)
300g mass, hua Shi Gao Ji Xin Zhi Cheng Co., ltd.), gradient eluting with (A) acetone (organic phase) - (B) 0.5% phosphoric acid water (aqueous phase, mass concentration) by 5% acetone (mobile phase A) 60min to 25% acetone (mobile phase B) and 320nm absorption wavelength by DAD ultraviolet detector, collecting fraction of protocatechuic acid according to detector chromatographic peak curve (collecting chromatographic peak) at a flow rate of mobile phase of 18deg.C with 25 mL/needle, rotary evaporating to dryness to obtain protocatechuic acid compound (product is analyzed by nuclear magnetism and high resolution mass spectrum structure, and is determined to be protocatechuic acid compound), and liquid chromatography analysis with purity of 96.68% and yield of 93.8%.
Comparative example 1
The difference from example 1 is that the non-radical modified silica gel (100-200 mesh) was used as a separation material, and the other conditions were the same as in example 1, and crude protocatechuic acid could not be obtained by enrichment, so that two-dimensional preparation, separation and purification could not be performed, and high-purity protocatechuic acid could not be obtained.
Comparative example 2
The difference from example 1 is that the one-dimensional separation filler adopts common octadecylsilane chemically bonded silica, the other preparation conditions are the same, the crude protocatechuic acid is prepared in one dimension, the purity of liquid phase analysis is 42.58%, and the yield is 44.9%.
The two-dimensional separation filler adopts common octadecylsilane chemically bonded silica gel, the rest preparation conditions are the same, and the purity of protocatechuic acid is 79.48 percent and the yield is 73.8 percent through liquid chromatography analysis.
Claims (5)
1. A method for preparing protocatechuic acid from Phellinus linteus medicinal material comprises the following steps:
(1) Boiling and extracting Phellinus linteus medicinal material with pure water to obtain Phellinus linteus water extract;
(2) Filtering the Phellinus linteus water extract with hollow fiber membrane to obtain membrane permeate;
(3) Carrying out one-dimensional enrichment on membrane permeate liquid by using pure water-resistant C8YE silica gel filler to obtain crude protocatechuic acid, wherein the used chromatographic filler is C8YE filler, the elution condition is that acetonitrile is an organic phase, acid water is an aqueous phase, the aqueous phase is one or two of acetic acid and phosphoric acid, and the ratio is 0.01-3.0%, v/v; according to the isocratic of 1-30 percent of the organic phase, the linear gradient or the step gradient of 1-30 percent, the flow rate of 0.01-1.0 times of the filler volume/min, the temperature of 15-55 ℃ and the sample loading amount of 0.2-6.0 percent expressed by the ratio of the solid mass of the sample solution to the filler mass, the detector is a DAD ultraviolet detector, the elution time is 40-300 min, fractions are collected according to the chromatographic peak curve of the detector, liquid phase analysis is carried out on all the fractions, the protocatechuic acid fractions are confirmed, and the mixture is concentrated to 10-300 mg/mL to prepare a protocatechuic acid crude product in one dimension; (4) Preparing a protocatechuic acid crude product in two dimensions by using a polar copolymerization C18HC bonded silica gel filler to obtain a high-purity protocatechuic acid product, wherein the elution condition is that acetone is an organic phase, acid water is an aqueous phase and is a mobile phase, the aqueous phase is formic acid or phosphoric acid, and the ratio of the aqueous phase to the formic acid or phosphoric acid is 0.05-3.0%, and v/v; according to the isocratic of 1-50% of the organic phase, the linear gradient or the step gradient of 1-50%, the flow rate of 0.02-1.2 times of the filler volume/min, the temperature of 15-55 ℃, the sample loading amount expressed by the ratio of the solid mass of the sample solution to the filler mass of 0.1-4%, the detector is a DAD ultraviolet detector, the elution time is 15-200 min, the components of protocatechuic acid are collected according to the chromatographic peak curve of the detector, and the obtained fraction is dried in vacuum, so that the protocatechuic acid product with the purity of more than 95% can be obtained.
2. The method of claim 1, wherein the Phellinus linteus medicinal material is extracted by pure water at a feed liquid ratio of 1:20-1:150, m/v, and soaked for 2-72 hours; heating and boiling for extraction for 1-20 hours, collecting water extract, repeatedly adding water for boiling and extracting solid materials according to the feed-liquid ratio of 1:20-1:150 and m/v, collecting water extract, repeatedly extracting for 1-6 times, and combining to obtain the water extract.
3. The method of claim 1, wherein the water extract is subjected to hollow fiber membrane filtration by a membrane filtration technology, and the hollow fiber membrane filter core has a molecular weight of 5000-1000000, so as to obtain the hollow fiber membrane water phase permeate.
4. The method of claim 1, wherein pure water resistant C8YE silica gel filler is adopted for one-dimensional preparation, so that the method has a good enrichment effect on protocatechuic acid, the hollow fiber membrane aqueous phase permeate can be subjected to large-volume direct loading enrichment, the filler has a particle size of 5-200 mm, the pore diameter is 50-300 a, and crude protocatechuic acid is obtained through enrichment.
5. The method of claim 1, wherein the two-dimensional preparation adopts chromatographic packing as C18HC silica gel packing of polar copolymerization bonding technology, which can well retain protocatechuic acid, has good orthogonality with one-dimensional separation, and can separate and remove small molecular organic impurities, thereby obtaining high-purity protocatechuic acid, wherein the used chromatographic packing has a particle size of 5-200 mm and a pore diameter of 50-300A, and the protocatechuic acid product with a purity of >95% is prepared.
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