CN103739656A - 28-O-beta-D-glucosyl phytolaccagenin, and preparation method and application thereof - Google Patents
28-O-beta-D-glucosyl phytolaccagenin, and preparation method and application thereof Download PDFInfo
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- CN103739656A CN103739656A CN201310748718.4A CN201310748718A CN103739656A CN 103739656 A CN103739656 A CN 103739656A CN 201310748718 A CN201310748718 A CN 201310748718A CN 103739656 A CN103739656 A CN 103739656A
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Abstract
The invention relates to the field of biological medicines, and particularly discloses a 28-O-beta-D-glucosyl phytolaccagenin (I) and a preparation method thereof by biotransforming phytolaccagenin by a strain with the collection number of NRRL1086. The invention also discloses application of the 28-O-beta-D-glucosyl phytolaccagenin in the anti-inflammatory aspect.
Description
Technical field
The present invention relates to bio-pharmaceutical field, be specifically related to 28-O-β-D-Glucose base esculentoside and preparation method thereof, the invention also discloses its anti-inflammatory aspect purposes.
Background technology
Inflammation is modal a kind of pathologic process in human diseases, with most of disease-relateds.Anti-inflammatory drug is the second largest class medicine that is only second to clinically anti-infectives, at present applying clinically more anti-inflammatory drug is mainly NSAID (non-steroidal anti-inflammatory drug) and adrenal cortex hormones drug, but these drug effects are many target spots, multipath, the dosage using and also have nothing in common with each other the course for the treatment of and various mechanism between also there is complicated cyberrelationship, life-time service can bring a lot of untoward reactions.Along with constantly developing and being familiar with and for many years clinical and experiment confirm Chinese medicine, a lot of Chinese medicine has good anti-inflammatory action, and toxic side effect is little and aboundresources, so the exploitation of traditional Chinese medicine monomer and structure of modification and the focus that the research of its pharmacological mechanism become to new drug development in the world today.Pentacyclic triterpenoid is distributed widely in each kind of plant, has biological activity widely, studies show that and aspect anti-inflammatory, has significant activity.As Phytolaccoside E has obvious anti-inflammatory action, but natural origin is few, and its aglycon obtains relatively simple, and activity is relatively poor, and poorly water-soluble, has affected the performance of its drug effect.Water-soluble in order to increase, keep simultaneously or increase its activity, it has been carried out to structural modification, chemosynthesis a large amount of derivatives, be wherein no lack of and have active good compound to find.But the glycosylation modified rare report of the microorganism of relevant american pokeweed root leaf and seed sapogenin.
Microbial transformation is to utilize the specific enzymes exogenous compound of microorganisms to carry out the specific biochemical reaction of structural modification.Microbial transformation has the three-dimensional arrangement selectivity of height, can the catalysis of single-minded ground specifically react, without loaded down with trivial details protection and deprotection, operate, and has advantages of efficient, environmental protection, is a kind of effective ways that natural radioactivity compound carries out structural modification.If introduce glycosyl in the Triterpenoids sapogenins class aglycon that contains carboxyl, can solve to a certain extent the poor problem of bioavailability, keep even increasing its activity simultaneously.
Summary of the invention
The invention discloses the compound of structural formula I:
Called after 28-O-β-D-Glucose base esculentoside.The present invention also comprises the solvate of the compound of structural formula I simultaneously.Its
13c-NMR data are: δ (ppm) C (1) 44.9, C (2) 71.6, C (3) 73.0, C (4) 42.4, C (5) 48.1, C (6) 18.3, C (7) 32.9, C (8) 40.0, C (9) 48.6, C (10) 37.2, C (11) 23.9, C (12) 123.7, C (13) 143.8, C (14) 42.4, C (15) 28.3, C (16) 23.5, C (17) 46.6, C (18) 43.2, C (19) 42.4, C (20) 43.9, C (21) 30.6, C (22) 34.0, C (23) 67.7, C (24) 14.5, C (25) 17.6, C (26) 17.4, C (27) 26.1, C (28) 28.5, C (29) 28.5, C (30) 177.0, with american pokeweed root leaf and seed sapogenin
13c-NMR data are compared, and can determine that its parent nucleus is american pokeweed root leaf and seed sapogenin, by the variation of chemical displacement value, can determine that sugar is to be connected in C
28on position.Also have in addition 6 Glucose Carbon signals, be respectively GLC (1) 95.8, GLC (2) 74.1, GLC (3) 78.9, GLC (4) 71.0, GLC (5) 762.0, GLC (6) 51.7.
Pharmacological testing proves, formula I compound of the present invention has excellent anti-inflammatory activity.
Formula I compound of the present invention preferably be take american pokeweed root leaf and seed sapogenin with bioconversion method and is transformed preparation as substrate, and method is as follows:
In order to find suitable conversion american pokeweed root leaf and seed sapogenin, become the bacterial classification of 28-O-β-D-Glucose base esculentoside, the present invention has screened a plurality of bacterial classifications altogether, found that, preserving number is that NRRL1086 bacterial classification has stronger conversion capability (in Table 2) to american pokeweed root leaf and seed sapogenin.
Screen liquid nutrient medium used (PDA): 200 grams of fresh peeling potatos add after boiling water 500mL boils 15min filters, and filtrate adds glucose 20g, KH
2pO
43.0g, MgSO
40.75g, Vb
110.0mg, adding distil water is settled to 1.0L, adds NaOH or HCl adjust pH to 6.0, every bottle of packing 30mL liquid nutrient medium of 150mL Erlenmeyer flask, 121 ℃, 0.15MPa sterilizing 20min.
During strain screening, preserve bacterial classification slant medium used and be the agar that adds 1.5% at aforesaid liquid substratum, the every pipe 5mL of 15mL tool plug test tube, makes after 121 ℃, 0.15MPa sterilizing 20min are cooling.
The preservation of bacterial classification and activation: actication of culture adopts two step activation methods, referring to: Nair, M.S.R., and Basile, D.V.Bioconversion of artenium B to artmisinn. natural product magazine (Jounal of Natural Products) 1993,56 (9): 1559.First bacterial classification is inoculated in to liquid nutrient medium, after 28 ℃ of 180r/min rotating and culturing 24-48h, transfers in another liquid nutrient medium, inoculum size 1-5%(V/V), with application of sample after condition cultivation 24h.
The preparation of sample and application of sample: american pokeweed root leaf and seed sapogenin is dissolved in ethanol, be made into 10mg/mL solution for standby; Every bottle of bacterium liquid (30mL) through two step activation adds 0.5mL sample solution, makes every bottle of bacterium liquid containing american pokeweed root leaf and seed sapogenin 5mg.With condition, cultivate after 120h, stopped reaction, filters thalline, and fermented liquid extracts 3～5 times by the ethyl acetate of equivalent, combining extraction liquid, recovery ethyl acetate; Be extracted medicinal extract, thalline extraction using alcohol 3 times, united extraction liquid, reclaims ethanol, obtains extracting medicinal extract, and two kinds of medicinal extract are merged, and adds a little acetic acid ethyl dissolution standby thin layer and identifies use.
Blank: blank is established positive control (substrate+substratum), negative control (substratum+bacterium), solvent control (substratum+bacterium+ethanol), cultivation and extraction conditions are the same.
The thin layer of converted product is identified:
Thin layer condition:
Thin layer plate: the silica gel G plate that 0.7% CMC-Na makes.
Developping agent: trichloromethane-methanol-water (7: 3: 1).
Developer: 10% sulfuric acid ethanol
Operation:
Transform extract and blank extract and put in thin layer plate respectively, ascending method is fully launched rear taking-up and is naturally dried, and spray is with 10% sulfuric acid ethanol, 105 ℃ of heating colour developings.Conversion results is in Table 2.
Table 2 microbial transformation esculentoside the selection result
| Bacterial classification | The selection result |
| Mucor sp. | — |
| Streptomyces sp. | — |
| Beauveria sp. | — |
| Rhizopus sp. | — |
| Gibberella sp. | — |
| NRRL-5646 | +++ |
| SC-2831 | — |
| SC-2831-DD | — |
| U1315-BN | — |
| Alternaria sp. | — |
| Alternaria sp. | — |
| Fusarium sp. | — |
| Phomopsis sp. | — |
| Phomopsis sp. | — |
| G.deliquescens. NRRL-1086 | +++ |
From the selection result, there are 2 kinds of bacterium to transform, NRRL 1086, and through measuring and calculating, transformation efficiency can reach 80%.And NRRL 5646 is not glycosylation conversion.Therefore, the present invention selects bacterial strain NRRL 1086, and the american pokeweed root leaf and seed sapogenin of take is prepared 28-O-β-D-Glucose base esculentoside as raw material.
The invention discloses a kind of preparation method of preparation I compound, is that NRRL 1086 bacterial strains carry out bio-transformation acquisition to american pokeweed root leaf and seed sapogenin with preserving number.
Preferred method is: take american pokeweed root leaf and seed sapogenin as substrate, utilize preserving number for the bacterial strain of NRRL 1086, substrate and this bacterial strain are cultivated altogether 3～8 days in substratum, termination reaction, with organic solvent extraction, concentrated extract, by silica gel column chromatography separation and get final product.
Wherein organic solvent is selected from one or more in ethyl acetate, chloroform, methylene dichloride, ethyl formate, butylacetate, toluene, normal hexane, propyl carbinol.More preferably ethyl acetate.
Silica gel column chromatography is separated carries out gradient elution with chloroform and methyl alcohol.
Substratum contains 10 ~ 30% potato decoction liquor, KH
2pO
4, MgSO
4, VITMAIN B1 and be selected from Portugal
One or more carbon sources in grape sugar, sucrose, bud sugar, starch, medium pH=5.0 ~ 7.0.Be weight percentage.
Wherein, by 100 milliliters of 20% potato decoction liquor, in substratum, the preferred content of each component is KH
2pO
4containing 0.1 ~ 0.5 gram; MgSO
4containing 0.05 ~ 0.5 gram; Glucose or sucrose 0.5-2.5 gram.
Highly preferred preparation method is: by preserving number be the bacterial strain of NRRL 1086 by inclined plane inoculating in liquid nutrient medium, put 28 ℃, rotating speed is to cultivate and within 24 hours, become seed liquor in the shaking table of 180r/m, and seed liquor continues to cultivate 24 hours after being forwarded to fermented liquid, adds conversion of substrate; Continuation is cultivated after 144 hours and is stopped catalyzed reaction, filters thalline, and fermented liquid extracts 5 times by the ethyl acetate of equivalent, and combining extraction liquid, recovery ethyl acetate, be extracted medicinal extract, and medicinal extract is column chromatography for separation after silica gel mixed sample; Take chloroform-methanol as elution system.Converted product, through recrystallizing methanol, obtains white powder converted product.
Pharmacological testing proves, structural formula I compound of the present invention has significant anti-inflammatory activity, is below test method and result:
The research of 28-O-β-D-Glucose base esculentoside anti-inflammatory activity
1, the impact of 28-O-β-D-Glucose base esculentoside p-Xylol induced mice ear swelling model
Get 50 of normal mouses, male and female half and half, are divided into 5 groups at random, are respectively control group, medication (25,50,100mg/kg) group, positive drug group (Naproxen Base 45mg/kg).Each organizes continuous gastric infusion three days, and once a day, control group gives the CMC-Na of respective volume.Last administration is only evenly smeared dimethylbenzene 20 μ L/ in the positive and negative two sides of left auricle after 40 minutes, within 20 minutes, post-tensioning neck is put to death, along auricle baseline, cut ears, with YLS-Q4 ear is swollen, makes ear device and sweep away auricle at the same position of left and right ear, weigh respectively, with the difference of self left and right auricle quality, represent swelling.
Inhibiting rate=[(control group swelling mean value-administration group swelling mean value)/control group swelling mean value] * 100%
Result is as follows:
| Group | Dosage mg/kg | Inhibiting rate | Statistical significance |
| Control group | - | - | - |
| Positive drug group | 45 | 45.7% | P＜0.01 |
| High dose group | 100 | 63.1% | P＜0.01 |
| Middle dosage group | 50 | 47.6% | P＜0.01 |
| Low dose group | 25 | 14.5% | P＜0.05 |
As can be seen here, 28-O-β-D-Glucose base esculentoside can suppress dimethylbenzene induced mice auricle acute inflammation, and has certain concentration dependent.
2,28-O-β-D-Glucose base esculentoside on Carrageenan causes the impact of rat paw edema model
Get 50 of normal male rats, be divided at random 5 groups, be respectively control group, medication (25,50,100mg/kg) group, positive drug group (Naproxen Base 30mg/kg).Each organizes continuous gastric infusion three days, and once a day, control group gives the CMC-Na of respective volume.Before last administration, with YLS-7B toes volume measuring apparatus, measure right back sufficient volume, as administration front volume V
0, administration, after 40 minutes, is injected 1% λ-carrageenin 0.1mL/ between whole sole of the foot stndon sheath and is only caused inflammation after Rat Right, and after causing inflammation, 1h, 3h, 5h, 7h measure right back sufficient volume V respectively
s, so that scorching forebody-afterbody product moment (V
s-V
0) be swelling.
Result is as follows:
| Group | Dosage mg/kg | 1h swelling/mL | 3h swelling/mL | 5h swelling/mL | 7h swelling/mL |
| Control group | - | 0.41±0.12 | 0.83±0.13 | 0.70±0.12 | 0.63±0.11 |
| Positive drug group | 30 | 0.08±0.07 * | 0.21±0.05 * | 0.13±0.08 * | 0.12±0.07 ** |
| High dose group | 100 | 0.08±0.05 ** | 0.18±0.04 * | 0.11±0.03 ** | 0.11±0.07 * |
| Middle dosage group | 50 | 0.14±0.05 ** | 0.37±0.12 ** | 0.33±0.05 * | 0.15±0.05 ** |
| Low dose group | 25 | 0.27±0.05 * | 0.52±0.06 ** | 0.42±0.07 * | 0.32±0.06 ** |
Compare with control group
*p < 0.05,
*p < 0.01
This shows, after medication, on Carrageenan causes rat paw edema restraining effect, and has certain concentration dependent.
3, the impact of 28-O-β-D-Glucose base esculentoside on rat AA model
Rat grouping, medication are the same, by same lot number 80 ℃ of water-bath 1h of bacille Calmette-Guerin vaccine deactivation, with sterilising liq paraffin, be made into the emulsion of 10g/L, being fully ground is Cheng Foshi Freund's complete adjuvant (FCA).Place 4 ℃ of Refrigerator stores standby, before use, shake up.With toes capacity measurer, measure and cause the scorching front rat following volume of left and right rear articulatio talocruralis (mL), then in the left back toes intradermal injection of every mouse 0.1mL FCA, cause inflammation, Normal group injection 0.1mL PBS.Cause scorching first 3 days gastric infusions.Respectively at cause scorching before and cause scorching after 6,12,18 and 24h, with the detection of toes capacity measurer, cause scorching forward and backward rat and cause scorching parapodum swelling, to observe AA rat primary pathology.
Result is as follows:
| Group | Dosage mg/kg | 6h swelling/mL | 12h swelling/mL | 18h swelling/mL | 24h swelling/mL |
| Control group | - | 0.49±0.06 | 0.54±0.07 | 0.64±0.07 | 0.50±0.06 |
| Positive drug group | 30 | 0.16±0.09 ** | 0.22±0.07 * | 0.29±0.08 ** | 0.28±0.06 ** |
| High dose group | 100 | 0.11±0.06 ** | 0.18±0.08 * | 0.27±0.07 ** | 0.25±0.06 * |
| Middle dosage group | 50 | 0.24±0.05 * | 0.33±0.08 * | 0.38±0.06 * | 0.35±0.07 ** |
| Low dose group | 25 | 0.41±0.05 ** | 0.49±0.08 ** | 0.53±0.13 * | 0.51±0.06 ** |
Compare with control group
*p < 0.05,
*p < 0.01
Each is organized rats with left foot 6h after causing inflammation and starts swelling, and 18h peaks.After medication, the AA rat primary inflammation of FCA induction is had to obvious restraining effect, and there is certain concentration dependent.
28-O-β-D-Glucose base esculentoside of the present invention can mix with pharmaceutically acceptable carrier, for the preparation of medicine for treatment compositions.Can be prepared into formulation general in pharmaceutics, as parenteral dosage forms such as the gastrointestinal administration formulations such as capsule, tablet, pill, oral liquid, granule, tincture, sustained release dosage and injection, transdermal patch, external preparations.
Embodiment
Embodiment 1
The preparation of 28-O-β-D-Glucose base esculentoside:
Substrate american pokeweed root leaf and seed sapogenin 200mg is dissolved in 20mL ethanol; The glucose solution 100mL of preparation 0.5g/mL, sterilizing (the same PDA of condition); Bacterial classification NRRL1086 by the solid inclined plane inoculating of 4 ℃ to liquid PDA substratum (substratum by 100 milliliter of 20% potato decoction liquor containing KH
2pO
40.3 gram; MgSO
40.75 gram; 10 grams of glucose; 0.01 gram of preparation of VITMAIN B1, liquid nutrient medium divides the triangular flask that is filled to 150mL, every bottled liquid 30mL), to cultivating 24 hours in shaking table, (28 ℃, 180r/m), be seed liquor; Seed liquor is transferred under aseptic condition in liquid PDA substratum (substratum forms the same), in shaking table, continues to cultivate 24 hours.Every bottle adds 1mL american pokeweed root leaf and seed sapogenin ethanolic soln and 3mL sucrose solution, cultivates termination reaction after 144 hours.Fermented liquid extracts 6 times by the ethyl acetate of equivalent, combining extraction liquid, recovery ethyl acetate; Be extracted medicinal extract 313mg, take 100-200 order silica gel 0.8g and residue and evenly mix sample, column chromatography 200～300 order 20g dry column-packings, chloroform-methanol gradient elution, in chloroform-methanol=85: in 15 eluting fraction, can obtain target converted product 28-O-β-D-Glucose base esculentoside, through recrystallizing methanol, obtain white powder 208mg.
Its carbon spectrum as mentioned above.
Embodiment 2
Tablet
Get 28-O-β-D-Glucose base esculentoside 100g and starch 50g that embodiment 1 makes, dextrin 50g mixes, and with appropriate 30% ethanol, makes wetting agent, makes softwood, and ordinary method is granulated, and adds appropriate Magnesium Stearate to mix, and makes tablet.
Claims (9)
1. the compound of structural formula I or its pharmaceutically acceptable solvate:
2. the compound of claim 1 or the preparation method of its pharmaceutically acceptable solvate, is characterized in that: with preserving number, be that NRRL1086 bacterial strain carries out bio-transformation acquisition to american pokeweed root leaf and seed sapogenin.
3. the preparation method of claim 2, wherein bioconversion method is as follows: take american pokeweed root leaf and seed sapogenin as substrate, utilize the bacterial strain that preserving number is NRRL1086, substrate and this bacterial strain are cultivated altogether 4 ~ 7 days in substratum, termination reaction, fermented liquid organic solvent extraction, concentrated extract, obtain medicinal extract, by silica gel column chromatography separation, obtain target compound.
4. the preparation method of claim 3, wherein organic solvent comprises: ethyl acetate, chloroform, methylene dichloride, ethyl formate, butylacetate, toluene, hexane, propyl carbinol etc.
5. the preparation method of claim 3, substratum is containing 10 ~ 30% potato decoction liquor, KH
2pO
4, MgSO
4, VITMAIN B1 and be selected from glucose, sucrose, bud sugar, starch one or more carbon source, medium pH=5.0 ~ 7.0.
6. the preparation method of claim 3, wherein by 100 milliliters of 20% potato decoction liquor, KH
2pO
40.1 ~ 0.5 gram; MgSO
40.05 ~ 0.5 gram; Glucose 0.5-2.5 gram (or sucrose 0.5-2.5 gram).
7. the preparation method of claim 2, wherein bacterial classification first activates before cultivation, soak time 20～30h.
8. a pharmaceutical composition, wherein contains compound or its pharmaceutically acceptable solvate and the pharmaceutically acceptable carrier of claim 1.
9. the compound of claim 1 or its pharmaceutically acceptable solvate are for the preparation of the purposes of anti-inflammatory drug.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106148472A (en) * | 2015-04-22 | 2016-11-23 | 中国科学院大连化学物理研究所 | A kind of method that enzymatic hydrolysis pokeroot saponin A prepares esculentoside second |
| CN110078783A (en) * | 2019-05-30 | 2019-08-02 | 江西省药品检验检测研究院 | Caulis akebiae saponin(e H and preparation method thereof |
-
2013
- 2013-12-31 CN CN201310748718.4A patent/CN103739656A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106148472A (en) * | 2015-04-22 | 2016-11-23 | 中国科学院大连化学物理研究所 | A kind of method that enzymatic hydrolysis pokeroot saponin A prepares esculentoside second |
| CN106148472B (en) * | 2015-04-22 | 2019-09-13 | 中国科学院大连化学物理研究所 | A kind of method that enzymatic hydrolysis pokeroot saponin A prepares esculentoside second |
| CN110078783A (en) * | 2019-05-30 | 2019-08-02 | 江西省药品检验检测研究院 | Caulis akebiae saponin(e H and preparation method thereof |
| CN110078783B (en) * | 2019-05-30 | 2021-07-23 | 江西省药品检验检测研究院 | Akebia saponin H and preparation method thereof |
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