CN112047983B - Paedenic acid monomer compound, preparation method and application thereof - Google Patents
Paedenic acid monomer compound, preparation method and application thereof Download PDFInfo
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- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
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Abstract
The invention provides a paederosidic acid monomer compound, a preparation method thereof and application thereof in preparing a medicament for reducing uric acid, wherein the paederosidic acid 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 ethanol eluate, and drying under reduced pressure to obtain herba Paederiae extract; c) Loading the herba Paederiae extract onto macroporous adsorbent resin chromatography, sequentially eluting with water and 5-30% ethanol, collecting 20% ethanol eluate or 5-10% ethanol eluate, concentrating, and drying to obtain herba Paederiae refined extract; and d) adding methanol into the refined paedera scandens extract for dissolving, filtering, collecting subsequent filtrate and crystallizing to obtain the paederosidic acid monomer compound.
Description
Technical Field
The invention relates to a paederoside acid 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 mainly comprises iridoid glycosides, flavones, triterpenes, steroids, phenylpropanoids, volatile oil and other natural products.
The applicant's previous chinese patent publication specifications CN104398619A, CN104435226A and CN104474068A disclose fevervine extract and its use in reducing uric acid, anti-inflammatory and anti-gout arthritis aspects. However, the above patent publication does not disclose the obtention of a monomeric compound of paederosidic acid.
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: paederosidic acid monomer compound. The paederosidic acid monomer compound isolated according to the method of the invention has a purity of more than 90% and demonstrates better in vitro uric acid lowering activity relative to paederosidic extract.
Paedestin acid is a known compound with CAS number 18842-98-3, and has the following chemical structure:
accordingly, in one aspect, the present invention provides a paederosidic acid monomer compound prepared by the following method:
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 onto macroporous adsorbent resin chromatography, sequentially eluting with water and 5-30% ethanol, collecting 20% ethanol eluate or 5-10% ethanol eluate, concentrating, and drying to obtain herba Paederiae refined extract; and
d) Adding methanol into the refined paedera scandens extract for dissolving, filtering, collecting subsequent filtrate and crystallizing to obtain the paederosidic acid monomer 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 sequentially with water and 85% ethanol, and the eluate of 85% ethanol is collected.
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, 5% ethanol, 10% ethanol and 15% ethanol in sequence, and the eluted part of 5% -10% ethanol is collected, concentrated and dried to obtain the refined extract of the fevervine herb.
According to a preferred embodiment of the present invention, the macroporous adsorbent resin in steps b) and c) is a neat resin model D101, manufactured by Cangzhou Bayonne adsorbent materials science and technology Limited.
The second aspect of the present invention provides a method for preparing a paederosidic acid monomer compound, comprising the steps of:
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 20% ethanol eluate or 5% -10% ethanol eluate, concentrating, and drying to obtain refined herba Paederiae extract; and
d) Adding methanol into the refined paederia scandens extract for dissolving, filtering, collecting secondary filtrate and crystallizing to obtain the paederia scandens acid monomer compound.
In a third aspect, the present invention provides the use of the paederosidic acid monomer compound in the preparation of a medicament for reducing uric acid.
The fourth aspect of the invention provides the application of the paederoside acid monomer compound in preparing a medicament for treating gouty arthritis.
The fifth aspect of the invention provides the use of the paederosidic acid monomer compound in the preparation of a medicament for treating hyperuricemia.
The preparation method of the paederosidic acid monomer compound has the advantages of simple process, reasonable design and little 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 paederosidic acid monomer compound is over 90 percent, the paederosidic acid monomer compound has more remarkable uric acid reducing effect (P < 0.05) on a rat with acute hyperuricemia in a 20mg/kg dose group compared with a paederosidic extract.
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 paederosidic acid monomer 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 fevernine monomer compound obtained in example 2 of the present invention.
FIG. 5 is a high performance liquid chromatogram of a Paederia scandens extract used in example 3 of the present invention;
FIG. 6 is a high performance liquid chromatogram of a paederosidic acid monomer compound obtained in example 3 of the present invention.
Detailed Description
The conditions for HPLC detection and analysis of the paederosidic acid monomer compounds of the following examples are as follows:
and (3) chromatographic column: wates Atlantis C18.6 x 250mm,5um
Fluidity: methanol Mobile phase A (%) Mobile phase (B)
0-20min 20-40 80-60
20-30min 40-60
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 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, 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 at a ratio of 1kg to resin), eluting with deionized water for 2BV, discarding eluate and water eluate, eluting with 85% ethanol for 6BV, collecting eluate of 85% ethanol, concentrating under reduced pressure at 60 deg.C to obtain thick extract, adding a proper amount of deionized water (about 1/7 times of the amount of the medicinal materials), loading the mixture onto D101 macroporous adsorption resin, wherein the column diameter-height ratio of the resin is 1.
Example 1:
350.66g of herba Paederiae extract (liquid chromatogram is shown in figure 1) obtained by the above comparative example is dissolved by adding 3000ml of deionized water, and is subjected to macroporous adsorbent resin column chromatography (column volume is 3000ml, column diameter is 10 cm) with sample flow rate of about 1BV/h, and deionized water, 20% ethanol, 25% ethanol and 30% ethanol are sequentially eluted for 5BV each with elution flow rate of about 5BV/h. Collecting the 20% ethanol elution part, concentrating under reduced pressure, and recovering solvent to dry to obtain herba Paederiae crude extract-1. Taking herba Paederiae crude extract-1, adding appropriate amount of deionized water for dissolving, performing macroporous adsorbent resin column chromatography (column volume 3000ml, column diameter 10 cm), sequentially eluting with deionized water, 5% ethanol, 10% ethanol, and 15% ethanol for 5BV. Collecting 5% ethanol eluate, concentrating under reduced pressure, recovering solvent to dry, dissolving in methanol, filtering, collecting filtrate, crystallizing to obtain crystal of paederosidic acid, wherein the sample detection chromatogram is shown in FIG. 2, and the content of external standard method is 96.25%. Comparison products: paederate acid (batch No. 14081810) Chenoponfu scientific development, inc.
Example 2:
taking 201.96g herba Paederiae extract (liquid chromatogram is shown in figure 3) obtained in the above comparative example, adding 2000ml deionized water for dissolving, and performing macroporous adsorbent resin column chromatography (column volume 7000ml, column diameter 12 cm), eluting with deionized water, 5% ethanol, 10% ethanol, 15% ethanol, 20% ethanol, 25% ethanol, and 30% ethanol for 5BV respectively. Collecting the eluted part of 5-10% ethanol, vacuum concentrating, and recovering solvent to dry. Dissolving the residue in deionized water, and performing macroporous adsorbent resin column chromatography (column volume 3000ml, column diameter 10 cm) with sample flow rate of about 1BV/h; eluting with deionized water, 5% ethanol, 10% ethanol and 15% ethanol at flow rate of 5BV/h for 5BV/h. Collecting 8% ethanol eluate, concentrating under reduced pressure, recovering solvent to dry, dissolving in methanol, filtering, collecting filtrate, crystallizing to obtain crystal of paederosidic acid, wherein the sample detection chromatogram is shown in FIG. 4, and the content of external standard method is 98.06%. Comparison products: paedenic acid (lot: 14081810) Chenopop scientific development Co., ltd.
Example 3:
collecting herba Paederiae extract (liquid chromatogram is shown in FIG. 5) 101.64g obtained in the above comparative example, adding deionized water 1000ml for dissolving, and performing macroporous adsorbent resin column chromatography (column volume is 3500ml, column diameter is 10 cm), with sample flow rate of about 1BV/h; sequentially eluting 5BV of deionized water, 5% ethanol, 10% ethanol, 15% ethanol, 20% ethanol, 25% ethanol and 30% ethanol at the flow rate of about 5BV/h. Collecting the eluted part of 5-10% ethanol, vacuum concentrating, and recovering solvent to dry. Dissolving the residue in deionized water, purifying with macroporous adsorbent resin column chromatography (column volume 3000ml, column diameter 10 cm), and eluting with deionized water, 5% ethanol, 10% ethanol, and 15% ethanol for 5BV. Collecting 8% ethanol eluate, concentrating under reduced pressure, recovering solvent to dry, dissolving in methanol, filtering, collecting filtrate, crystallizing to obtain crystal which is paederosidic acid, and the content determination by external standard method is 92.12%. Comparison products: paederate acid (batch No. 14081810) Chenoponfu scientific development, inc.
Example 4: uric acid reduction experiment of paederosidic acid 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: paedenoic acid obtained in example 1
The source is as follows: shanghai institute of pharmaceutical industry
Lot number and specification: 170228;
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: 20mg/kg;
route of administration and volume: gavage, and dosing according to 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 a dosage: 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 (Shanghai) 2014-40018
1.3.2 animal Specifications
SPF grade SD rat, 6-8 weeks old, 180-220g.
1.3.3 sex and number
And 36 males.
1.3.4 animal feeding
SPF-grade environmental animal laboratory, laboratory animals use license numbers: SYXK (Shanghai) 2014-0018. All animals were fed standard SPF grade complete rat feed purchased from shanghai selideke experimental animals center of chinese academy of sciences. 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 cages are sterilized by autoclaving after being cleaned.
2. Experimental method
2.1 pharmaceutical formulation
(1) And (3) test drug configuration: the monomeric compound of Paederia scandens obtained in example 1 was dissolved in 0.9% physiological saline to prepare a suspension at a dose of 20mg/kg, and stored in a refrigerator at 4 ℃ for further use.
(2) Potassium oxonate suspension: potassium Oxonate powder was mixed with 0.9% physiological saline at a dose of 300mg/kg to prepare a suspension, which was 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 randomly assigned to 6 groups of 6 animals each after 1 week of acclimatization. The groups are normal control group, model group, positive medicine group, and 20mg/kg dosage group.
2.2.2 Molding and administration
After grouping, except for the normal group, the rats in other groups are administrated with oteracil potassium suspension (1 ml/mouse) in the abdominal cavity, and are administrated by gastric gavage after 1h interval, and the rats in the normal and model groups are administrated with normal saline with the same volume.
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 paederia scandens monomer compound obtained in the embodiment 1 of the invention on the SUA (acute hyperuricemia) caused by potassium oxonate
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 < 0.001), and the modeling is successful; the positive allopurinol has an extremely obvious inhibiting effect on the increase of SUA (P is less than 0.01) caused by the increase of endogenous uric acid, and the paederosidic acid obtained in the embodiment 1 of the invention has an obvious uric acid reducing effect (P is less than 0.05) on a 20mg/kg dose group of rats with acute hyperuricemia.
Claims (4)
1. A method for preparing a paederosidic acid monomeric compound, comprising the steps of:
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 paederia scandens extract to a macroporous adsorption resin for chromatography, eluting with water and 5-30% ethanol in sequence, collecting a 20% ethanol elution part or a 5-10% ethanol elution part, concentrating and drying to obtain a residue, adding water to the residue for dissolving, performing macroporous adsorption resin column chromatography again, eluting with deionized water, 5% ethanol, 10% ethanol and 15% ethanol in sequence, collecting a 5-10% ethanol elution part, concentrating and drying to obtain a paederia scandens refined extract; and
d) Adding methanol into the refined paederia scandens extract for dissolving, filtering, collecting secondary filtrate and crystallizing to obtain the paederia scandens acid 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 the macroporous adsorbent resin in steps b) and c) is of type D101.
4. The method of claim 1, wherein the concentration of methanol in step d) is greater than or equal to 95%.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101637475A (en) * | 2008-07-29 | 2010-02-03 | 上海医药工业研究院 | Application of paederoside acid or plant extract containing same |
| CN101890033A (en) * | 2009-05-20 | 2010-11-24 | 苏州颐华生物医药技术有限公司 | Application of paederosidic acid used for preparing analgesic drugs and/or anti-inflammatory drugs |
| 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 |
| CN104435226A (en) * | 2014-11-06 | 2015-03-25 | 宁波大昌药业有限公司 | Paederia scandens extract and application thereof |
| CN105348338A (en) * | 2015-10-15 | 2016-02-24 | 海南师范大学 | Method for extracting and separating paederosidic acid from Saprosma merrillii Lo |
-
2019
- 2019-06-05 CN CN201910487002.0A patent/CN112047983B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101637475A (en) * | 2008-07-29 | 2010-02-03 | 上海医药工业研究院 | Application of paederoside acid or plant extract containing same |
| CN101890033A (en) * | 2009-05-20 | 2010-11-24 | 苏州颐华生物医药技术有限公司 | Application of paederosidic acid used for preparing analgesic drugs and/or anti-inflammatory drugs |
| 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 |
| CN104435226A (en) * | 2014-11-06 | 2015-03-25 | 宁波大昌药业有限公司 | Paederia scandens extract and application thereof |
| CN105348338A (en) * | 2015-10-15 | 2016-02-24 | 海南师范大学 | Method for extracting and separating paederosidic acid from Saprosma merrillii Lo |
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| "鸡屎藤中环烯醚萜化合物的制备与鉴定";陈劲松 等;《西南民族大学学报 自然科学版》;20100930;第36卷(第5期);第777-779页 * |
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