CN112047988B - Paederoside monomer compound, preparation method and application thereof - Google Patents
Paederoside monomer compound, preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a paederoside monomer compound, a preparation method thereof and application thereof in preparing a medicament for reducing uric acid, wherein the paederoside monomer compound is prepared by the following steps: a) Extracting herba Paederiae with ethanol to obtain extractive solution; b) Concentrating the extracting solution until no alcohol smell exists, performing macroporous adsorption resin chromatography, sequentially eluting with water and 80-90% ethanol, collecting eluent, and drying under reduced pressure to obtain herba Paederiae extract; c) Loading the paederia scandens extract to macroporous adsorption resin chromatography, eluting with water and 5% -30% ethanol in sequence, collecting 15% -20% ethanol elution part, concentrating and drying to obtain refined paederia scandens extract; and d) carrying out fast column chromatography on the refined extract of the paederia scandens, eluting by using methanol, water or acetonitrile, water as an elution solvent, collecting the elution part of 15-16% of methanol or 8-86% of acetonitrile, and drying under reduced pressure to obtain the paederia scandens glycoside monomeric compound.
Description
Technical Field
The invention relates to a paederoside monomer compound, a preparation method and application thereof.
Background
Paederia scandens (Lour.) Merr is aerial part or whole plant of Paederia scandens of Rubiaceae, also called herba Paederiae and caulis Kadsurae Longipedunculatae. The paederia scandens is sweet and sour in taste and neutral in nature, enters liver, stomach and large intestine channels, has the effects of promoting digestion, removing food retention, dispelling wind, activating blood circulation, relieving pain and diminishing swelling, is mainly distributed in the southeast coastal areas of China, yangtze river watershed regions and the like, and is a traditional Chinese medicinal material. Modern pharmacological research proves that the Chinese fevervine herb has a plurality of remarkable effects of resisting inflammation, easing pain, calming, treating digestive system diseases and the like. The paederia scandens comprises iridoid glycosides, flavones, triterpenes, steroids, phenylpropanoids, volatile oil and other natural products.
Chinese patent publication nos. CN104398619A, CN104435226A and CN104474068A by the applicant disclose paederia scandens extracts and their use in reducing uric acid, anti-inflammatory and anti-gouty arthritis etc. However, the above patent publication does not disclose the obtention of a monomeric compound of paederoside.
Disclosure of Invention
The invention further separates and identifies a monomer compound from the Chinese fevervine herb extract on the basis of the patent publication specification: a paederoside monomer compound. The paederoside monomer compound isolated according to the method of the invention has a purity of more than 90%, and proves to have better in vitro uric acid reducing activity relative to paederoside extract.
Paederoside is a known compound with CAS number 20547-45-9, having the following chemical structure:
accordingly, in one aspect, the present invention provides a paederoside monomeric compound prepared by the following method:
a) Extracting herba Paederiae with ethanol to obtain extractive solution;
b) Concentrating the extract until no alcohol smell exists, performing macroporous adsorption resin chromatography, sequentially eluting with water and 80-90% ethanol, collecting eluate, and drying under reduced pressure to obtain herba Paederiae extract;
c) Loading the herba Paederiae extract into macroporous adsorbent resin chromatography, sequentially eluting with water and 5% -30% ethanol, collecting 15% -20% ethanol eluate, concentrating, and drying to obtain herba Paederiae refined extract; and
d) And (2) carrying out flash column chromatography on the refined extract of the paederia scandens, eluting by using methanol, water or acetonitrile, water as an eluting solvent, collecting an elution part of 15-16% of methanol or an elution part of 8-86% of acetonitrile, and drying under reduced pressure to obtain the paederia scandens glycoside monomeric compound.
According to a preferred embodiment of the invention, the amount ratio of the Chinese fevervine herb to the resin is 1kg of herb, and 300ml of macroporous resin after swelling pretreatment by absolute ethyl alcohol is needed.
According to a preferred embodiment of the invention, the elution in step b) is carried out with water and 85% ethanol in sequence, and the 85% ethanol eluate is collected.
According to a preferred embodiment of the invention, the elution in step c) is carried out with water, 5% ethanol, 10% ethanol, 15% ethanol, 20% ethanol, 25% ethanol and 30% ethanol in sequence.
According to a preferred embodiment of the present invention, the elution procedure in step d) with methanol to water as elution solvent is 15% methanol 5BV → 15% -16% methanol 3BV → 16% -100% methanol 0.01BV → 100% methanol 5BV.
According to a preferred embodiment of the present invention, the elution procedure in step d) with acetonitrile to water as elution solvent is 8% acetonitrile 3BV → 8% -86% acetonitrile 5BV → 100% acetonitrile 3BV.
According to a preferable embodiment of the invention, the residue obtained after drying under reduced pressure in step d) is added with methanol for redissolving, filtered, and the subsequent filtrate is collected, and the solvent is recovered under reduced pressure until dried, thus obtaining the paederoside monomer compound. According to a particularly preferred embodiment of the invention, the methanol concentration is equal to or greater than 95%, most preferably pure methanol.
According to a preferred embodiment of the present invention, the macroporous adsorbent resin in steps b) and c) is a neat grade resin with model number D101, manufactured by cangzhou baien adsorbent materials technologies ltd.
According to a preferred embodiment of the invention, the residue obtained after the concentration and drying in the step c) is dissolved in water, and then the residue is subjected to macroporous adsorption resin column chromatography again, and then eluted by deionized water, 10% ethanol, 15% ethanol and 20% ethanol in sequence, the eluted part of the 15% ethanol is collected, and the extract is concentrated under reduced pressure, and the solvent is recovered to be dry, so that the refined paederia scandens extract is obtained.
According to a preferable embodiment of the invention, the residue obtained after the concentration and drying in the step c) is dissolved in water, and the residue is subjected to macroporous adsorption resin column chromatography again, and then eluted by deionized water, 10% ethanol, 15% ethanol and 20% ethanol in sequence, and the eluted part of 20% ethanol is collected, concentrated under reduced pressure, and the solvent is recovered to be dry, so as to obtain the refined paederia scandens extract.
According to a preferred embodiment of the present invention, the column diameter height ratio of the macroporous adsorbent resin in step b) is 1.
According to a preferred embodiment of the invention, the sample loading flow rate in step b) is between 1.0 and 2.0BV/h and the elution flow rate is between 4 and 6BV/h.
The second aspect of the present invention provides a method for preparing a paederoside monomer compound, comprising the steps of:
a) Extracting herba Paederiae with ethanol to obtain extractive solution;
b) Concentrating the extract until no alcohol smell exists, performing macroporous adsorption resin chromatography, sequentially eluting with water and 80-90% ethanol, collecting eluate, and drying under reduced pressure to obtain herba Paederiae extract;
c) Loading the paederia scandens extract to macroporous adsorption resin chromatography, eluting with water and 5% -30% ethanol in sequence, collecting 15% -20% ethanol elution part, concentrating and drying to obtain refined paederia scandens extract; and
d) And (2) carrying out flash column chromatography on the refined extract of the paederia scandens, eluting by using methanol, water or acetonitrile, water as an eluting solvent, collecting an elution part of 15-16% of methanol or an elution part of 8-86% of acetonitrile, and drying under reduced pressure to obtain the paederia scandens glycoside monomeric compound.
The third aspect of the invention provides the application of the paederoside monomer compound in preparing a medicament for reducing uric acid.
The fourth aspect of the invention provides the application of the paederoside monomer compound in preparing a medicament for treating gouty arthritis.
The fifth aspect of the invention provides the application of the paederoside monomer compound in preparing a medicament for treating hyperuricemia.
The preparation method of the paederoside monomer compound has the advantages of simple process, reasonable design and small environmental pollution. The method has no pollution to the environment, the use amount of ethanol and methanol is less, the cost is lower, the yield is higher, and the method is suitable for industrial production.
Because the purity of the paederia scandens monomer compound is higher than 90%, compared with a paederia scandens extract, the paederia scandens monomer compound has a more remarkable uric acid reducing effect on acute hyperuricemia rats, and shows a certain dose dependence relationship.
Drawings
FIG. 1 is a high performance liquid chromatogram of a Paederia scandens extract used in example 1 of the present invention;
FIG. 2 is a high performance liquid chromatogram of a paederia scandens monomeric compound obtained in example 1 of the present invention;
FIG. 3 is a high performance liquid chromatogram of a Paederia scandens extract used in example 2 of the present invention;
FIG. 4 is a high performance liquid chromatogram of the monomeric compound of paederoside obtained in example 2 of the present invention.
Detailed Description
The conditions of HPLC analysis of the monomeric compounds of paederoside in the following examples are as follows:
a chromatographic column: wates Atlantis C184.6 x 250mm,5um
Fluidity: acetonitrile as mobile phase A (%) 0.1% phosphoric acid water as mobile phase (B),
the elution procedure was as follows:
0-25min 15→25 85→75
flow rate: 1ml/min; column temperature: 30 ℃; detection wavelength: 235nm.
Comparative example (Paederia scandens extract obtained in example 1 of CN104435226A was further refined):
taking a Yunnan fevervine herb (batch number: 150830) adding 8 times of 95% ethanol, reflux extracting for 3 hr, extracting for 3 times, filtering, mixing extractive solutions, concentrating under reduced pressure at 60 deg.C until no alcohol smell exists, adding deionized water to 4L for dissolving, centrifuging, collecting supernatant, subjecting to D101 macroporous adsorbent resin (D101 resin obtained by swelling with anhydrous ethanol and swelling with 300ml of medicinal material to resin at a ratio of 1kg to 1 kg), eluting with deionized water for 2BV, discarding eluate and water eluate, eluting with 85% ethanol for 6BV, collecting 85% ethanol eluate, concentrating under reduced pressure at 60 deg.C to obtain soft extract, adding a proper amount of deionized water (about 1/7 times of the amount of the medicinal materials), loading the mixture on D101 macroporous adsorption resin, wherein the height ratio of the resin column diameter is 1.
Example 1:
taking 201.96g of the paederia scandens extract (the liquid phase map of which is shown in figure 1) obtained in the comparative example, adding 2000ml of deionized water for dissolving, carrying out column chromatography through macroporous adsorption resin (the column volume is 7000ml, the diameter-height ratio is 1 BV/h), and eluting 5BV of deionized water, 5% ethanol, 10% ethanol, 15% ethanol, 20% ethanol, 25% ethanol and 30% ethanol in sequence respectively at the sample loading flow rate of 1 BV/h. Collecting 15% -20% ethanol elution part, concentrating under reduced pressure, and recovering solvent to dry. Dissolving the residue in deionized water, performing macroporous adsorbent resin column chromatography (3500 ml column volume, 10cm column diameter, height ratio of 1: 12), eluting with deionized water, 10% ethanol, 15% ethanol, and 20% ethanol at a flow rate of 1BV/h for 3BV each. Collecting 15% ethanol eluate, concentrating under reduced pressure, and recovering solvent to dry to obtain herba Paederiae refined extract-1. Extract-1 was extracted from fevervine scandens, purified by flash preparative apparatus (Biotage Isolera One, biotage, sweden) and purified by flash column chromatography (sepaflame semi-chromatographic C18, 50um,
100g, santai technologies, inc.), the elution solvent is methanol, water; the elution procedure was: 15% methanol 5BV → 15% -16% methanol 3BV → 16% -100% methanol 0.01BV → 100% methanol 5BV; monitoring the wavelength at 230nm and the flow rate at 50ml/min, and collecting the part with higher absorption value intensity of the elution peak of 15-16% methanol. Recovering solvent under reduced pressure to dry, adding methanol for redissolving, filtering, collecting filtrate, and recovering solvent under reduced pressure to dry to obtain paederoside monomer compound. The detection spectrum is shown in figure 2, and the purity is 96.92 percent by an area normalization method.
Example 2:
taking 201.96g of the fevervine herb extract (the liquid phase chromatogram of which is shown in figure 3) obtained in the comparative example, adding 2000ml of deionized water for dissolving, carrying out column chromatography by macroporous adsorption resin (the column volume is 7000ml, the diameter-height ratio is 1 BV/h), and eluting 5BV of deionized water, 5% ethanol, 10% ethanol, 15% ethanol, 20% ethanol, 25% ethanol and 30% ethanol in sequence respectively at the sample loading flow rate of 1 BV/h. Collecting 15% -20% ethanol eluate, concentrating under reduced pressure, and recovering solvent to dry. Dissolving the residue in deionized water, performing macroporous adsorbent resin column chromatography (3500 ml column volume, 1:10 diameter/height ratio) at a flow rate of 1BV/h, and eluting with deionized water, 10% ethanol, 15% ethanol and 20% ethanol for 3BV. Collecting the 20% ethanol eluate, concentrating under reduced pressure, and recovering solvent to dry to obtain herba Paederiae refined extract-2. Taking Paederia scandens refined extract-2, passing through a flash preparation instrument (Biotage Isolera One, biotage company) by a flash chromatography column (Biotage SNAP card KP-C18-HS 30g, biotage technologies, inc.), and eluting with acetonitrile: water; the elution procedure was: 8% acetonitrile 3BV → 8% -86% acetonitrile 5BV → 100% acetonitrile 3BV; monitoring the wavelength of 230nm and the flow rate of 50ml/min, and collecting the part with higher absorption value intensity of 8-86% acetonitrile elution peak. Recovering solvent under reduced pressure to dry, adding methanol for redissolving, filtering, collecting filtrate, and recovering solvent under reduced pressure to dry to obtain paederoside monomer compound. The detection pattern is shown in FIG. 4, and the purity measured by the area normalization method is 93.68%.
Example 3: uric acid reduction experiment of paederia scandens monomer compound for treating rat acute hyperuricemia model caused by potassium oxonate
1. Instruments and materials
1.1 test drugs
1.1.1 samples
Name/abbreviated number: paederoside monomeric compound obtained in example 1
The source is as follows: shanghai institute of pharmaceutical industry
Lot number and specification: 181110;
traits and storage conditions: white powder with purity more than 90 percent is stored in a sealed way at low temperature and in dark place;
the preparation method of the medicine comprises the following steps: diluting with normal saline;
designing the dose: the low dose is 20mg/kg, and the high dose is 40mg/kg;
route of administration and volume: and (4) intragastric administration, and dosing according to the weight conversion.
1.1.2 Positive control
Name/abbreviated number: allopurinol tablets;
the source is as follows: shanghai Xin Wanxiang pharmaceutical Co., ltd;
lot number and specification: (110802), 100 mg;
traits and storage conditions: tablets are dried and stored at room temperature;
designing the dose: 50mg/kg;
route of administration and volume: gavage, and dosing according to weight conversion.
1.2 instruments and reagents
1.2.1 Experimental instruments
(1) Electronic analytical balance, model number: sartorius ALC-210.3, manufacturer: sadolis corporation;
(2) High-speed centrifuge, model: 5810R, manufacturer: eppendorf (germany);
(3) Full-automatic serum biochemical analyzer, model: 7080, manufacturer: calendar (japan);
(4) Mouse scale, manufacturer: nanjing, ma Nenli pharmaceutical instruments, inc.;
1.2.2 Experimental reagents
A molding agent: potassium Oxonate (Adamas Reagent Co., ltd.; LOT: P1275208);
solvent: physiological saline.
1.3 animals
1.3.1 animal sources
Strains and species: SD rat
Animal quality certification number: 2015000550327
Providing a unit: shanghai Si Laike laboratory animal responsibility Co., ltd
Production license: SCXK (Shanghai) 2015-0005
The unit of use: shanghai institute of pharmaceutical industry
The use license: SYXK 2014-40018
1.3.2 animal Specification
SPF grade SD rats, 6-8 weeks old, 180-220g.
1.3.3 gender and number
And 36 males.
1.3.4 animal feeding
SPF grade environmental animal laboratory, laboratory animals use license numbers: SYXK (Shanghai) 2014-0018. Animals were fed standard SPF-grade complete rat feed purchased from the experimental animal center of shanghai seliaceae, chinese academy. Drinking water for animals is supplied by drinking bottles, and the animals can drink water freely. 10-15 animals are raised in each cage, the room temperature of the animals is set to be 20-22 ℃, the humidity is set to be 40-70%, and the animals are alternately illuminated in light and shade for 12 hours. The padding is replaced at least 2 times per week, the feeding box is replaced at the same time, and the feeding box is replaced at any time when abnormal conditions occur. The sterilized drinking bottle and the bottle stopper are replaced every day, and the cage is sterilized for 1 time every two weeks. All the replaced and washed cages are sterilized by high pressure after being washed.
2. Experimental methods
2.1 pharmaceutical formulation
(1) Test agent configuration: the monomeric compound of paederoside obtained in example 1 is dissolved in 0.9% physiological saline, prepared into suspensions with corresponding concentration according to different dosages, and stored in a refrigerator at 4 ℃ for later use.
(2) Potassium oxonate suspension: potassium oxonate powder is prepared into suspension by 0.9 percent of physiological saline according to the dosage of 300mg/kg, and the suspension is prepared on the day of the experiment.
(3) Allopurinol suspension: preparing a suspension according to the dosage of 50mg/kg, and preparing the preparation method as the same as the step (1).
2.2 Molding and grouping
2.2.1 animal groups
Animals were randomized into 6 groups of 6 animals each after 1 week of acclimatization. The groups are normal control group, model group, positive medicine group, and high and low dosage groups of the tested medicine.
2.2.2 Molding and administration
After grouping, except for the normal group, the rats in other groups are subjected to intraperitoneal administration of potassium oxonate suspension (1 ml/mouse), and are subjected to intragastric administration after 1h interval, and the rats in the normal and model groups are subjected to isovolumetric administration of normal saline.
2.2.3 index detection
Collecting blood from rat fundus venous plexus 1h after administration, centrifuging the obtained whole blood at 12000rpm for 5min to separate serum, and inspecting with a Nitarian serum biochemical detector to detect the change of Uric Acid (UA) content in serum.
3. Results of the experiment
The influence of the paederoside monomer compound obtained in the embodiment 1 on the SUA (acute hyperuricemia) caused by potassium oxonate
Comparison with the normal group: # P＜0.05， ## P＜0.01， ### p is less than 0.001; comparison with model groups: * P＜0.05， ** P＜0.01
the results are shown in the table, the blood uric acid concentration of the rat in the model group is very different from that of the normal control group (P is less than 0.001), and the modeling is successful; the allopurinol which is a positive drug has extremely obvious inhibition effect (P is less than 0.001) on the increase of the SUA caused by the increase of the endogenous uric acid, and the paederoside monomer compound has obvious uric acid reduction effect (P is less than 0.01) on low and high dose groups of rats with acute hyperuricemia and shows a certain dose dependence relationship.
The influence of the paederoside monomer compound obtained in the embodiment 2 on SUA (SUA) caused by potassium oxonate in acute hyperuricemia
Comparison with normal group: # P<0.05， ## P<0.01， ### P<0.001; comparison with model groups: * P<0.05，**P<0.01
The results are shown in the table, the blood uric acid concentration of the rats in the model group is very significantly different from that of the rats in the normal control group (P is less than 0.001), and the model building is successful; the positive allopurinol has a very obvious inhibiting effect (P is less than 0.001) on the SUA rise caused by the endogenous uric acid rise, and the paederoside monomer compound has a remarkable uric acid reducing effect (P is less than 0.05) on a 20mg/kg dose group of rats with acute hyperuricemia.
Claims (5)
1. A method for preparing a paederoside monomeric compound, which comprises the following steps:
a) Extracting herba Paederiae with ethanol to obtain extractive solution;
b) Concentrating the extracting solution until no alcohol smell exists, performing macroporous adsorption resin chromatography, sequentially eluting with water and 80-90% ethanol, collecting ethanol eluate, and drying under reduced pressure to obtain herba Paederiae extract;
c) Loading the herba Paederiae extract into macroporous adsorbent resin chromatography, sequentially eluting with water and 5% -30% ethanol, collecting 15% -20% ethanol eluate, concentrating, and drying to obtain herba Paederiae refined extract; and
d) Performing flash column chromatography on the paederia scandens refined extract, wherein an elution procedure with methanol and water as an elution solvent is 15% methanol 5BV → 15% -16% methanol 3BV → 16% -100% methanol 0.01BV → 100% methanol 5BV, or an elution procedure with acetonitrile and water as an elution solvent is 8% acetonitrile 3BV → 8% -86% acetonitrile 5BV → 100% acetonitrile 3BV, collecting 15% -16% methanol elution parts or 8% -86% acetonitrile elution parts, performing reduced pressure drying to obtain residues, adding methanol to the residues for redissolution, filtering, collecting a subsequent filtrate, and performing reduced pressure evaporation to dryness to obtain the paederia scandens monomer compound.
2. The method of claim 1, wherein the elution in step b) is sequentially performed with water and 85% ethanol, and the 85% ethanol eluate is collected.
3. The method of claim 1, wherein step c) is performed by eluting with water, 5% ethanol, 10% ethanol, 15% ethanol, 20% ethanol, 25% ethanol, and 30% ethanol in sequence.
4. The method of claim 1, wherein the concentration of methanol is greater than or equal to 95%.
5. The method of claim 1, wherein the macroporous adsorbent resin in steps b) and c) is of type D101.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101049360A (en) * | 2007-05-10 | 2007-10-10 | 周兰兰 | Preparation of Chinese traditional medicine for treating gout disease, and application of extractive of Chinese feveruine |
| CN101129524A (en) * | 2007-09-18 | 2008-02-27 | 蒋毅 | Paederia extractive and medical use of the same |
| CN101991592A (en) * | 2009-08-14 | 2011-03-30 | 上海颐华生物医药有限公司 | Application of paederoside to preparation of analgesic and/or anti-inflammatory medicaments |
| CN102344474A (en) * | 2011-07-26 | 2012-02-08 | 苏州宝泽堂医药科技有限公司 | Preparation method of paederia scandens glucoside |
| CN102846784A (en) * | 2011-06-23 | 2013-01-02 | 宁波大昌药业有限公司 | Paederia scandens water extract, and preparation method and application thereof |
| CN104072554A (en) * | 2014-06-16 | 2014-10-01 | 南京泽朗医药科技有限公司 | Method for extracting paederia scandens from fevervine |
| CN104435226A (en) * | 2014-11-06 | 2015-03-25 | 宁波大昌药业有限公司 | Paederia scandens extract and application thereof |
-
2019
- 2019-06-05 CN CN201910486995.XA patent/CN112047988B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101049360A (en) * | 2007-05-10 | 2007-10-10 | 周兰兰 | Preparation of Chinese traditional medicine for treating gout disease, and application of extractive of Chinese feveruine |
| CN101129524A (en) * | 2007-09-18 | 2008-02-27 | 蒋毅 | Paederia extractive and medical use of the same |
| CN101991592A (en) * | 2009-08-14 | 2011-03-30 | 上海颐华生物医药有限公司 | Application of paederoside to preparation of analgesic and/or anti-inflammatory medicaments |
| CN102846784A (en) * | 2011-06-23 | 2013-01-02 | 宁波大昌药业有限公司 | Paederia scandens water extract, and preparation method and application thereof |
| CN102344474A (en) * | 2011-07-26 | 2012-02-08 | 苏州宝泽堂医药科技有限公司 | Preparation method of paederia scandens glucoside |
| CN104072554A (en) * | 2014-06-16 | 2014-10-01 | 南京泽朗医药科技有限公司 | Method for extracting paederia scandens from fevervine |
| CN104435226A (en) * | 2014-11-06 | 2015-03-25 | 宁波大昌药业有限公司 | Paederia scandens extract and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| "LC-MS /MS 同时测定鸡矢藤提取物中4 个主要有效成分的含量";谢艳香 等;《中国实验方剂学杂志》;20180930;第24卷(第18期);第57-62页 * |
| "鸡矢藤提取物对尿酸钠诱导的大鼠急性痛风性关节炎的影响";胡寒 等;《中国医药工业杂志》;20181231;第49卷(第2期);第213-218页 * |
| "鸡矢藤的研究进展";王鑫杰 等;《世界临床药物》;20121231;第33卷(第5期);第303-310页 * |
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