CN104497005A - Swertiamarin thermal conversion product, as well as preparation method, preparation and application thereof - Google Patents
Swertiamarin thermal conversion product, as well as preparation method, preparation and application thereof Download PDFInfo
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- CN104497005A CN104497005A CN201410839888.8A CN201410839888A CN104497005A CN 104497005 A CN104497005 A CN 104497005A CN 201410839888 A CN201410839888 A CN 201410839888A CN 104497005 A CN104497005 A CN 104497005A
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- swertiamarin
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
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Abstract
The invention discloses a swertiamarin thermal conversion product, as well as a preparation method and an application thereof. The swertiamarin thermal conversion product is prepared from swertiamarin as a raw material through heating conversion, elution, separation and purification; and the swertiamarin thermal conversion product contains false Chinese swertia herb lactone composition with the weight percent being over 60%. The method disclosed by the invention is simple and convenient to operate and low in cost; the problems that a false Chinese swertia herb lactone component is low in content in plants, and cannot be greatly obtained easily through chemical synthesis due to a complicated molecular structure are solved. Compared with swertiamarin, the swertiamarin thermal conversion product obtained by the method is relatively high in hepatoprotective activity and anti-HBV activity, and can be applied to prevention and treatment of related hepatitis diseases.
Description
Technical field
The invention belongs to field of pharmaceutical chemistry technology, be specifically related to a kind of swertiamarin thermal transition product and preparation method thereof and application.
Background technology
Herba Swertiae bimaculatae lactone be the many chiralitys of a class, high oxidation, high thick and complex construction natural product, majority has anti-hepatitis B virus activities, is in recent years separated from Antihepatitis medicament Mile Swertia Herb and obtains.This constituents is very humble at plant materials content, does not possess industrialization production and commercial applications value, because its complex structure does not also obtain by chemosynthesis.
Chinese patent (application number is 201010587969.5) " swerilactone H-K; its medical composition and its use " discloses the Preparation method and use of 4 Herba Swertiae bimaculatae lactone compounds: by after Mile Swertia Herb herb drying and crushing by the easy refluxing extraction of ethanol, suspend in water after extracting solution concentrating under reduced pressure, use sherwood oil, ethyl acetate and n-butanol extraction successively, ethyl acetate portion is used repeatedly through silica gel column chromatography, separation obtains 4 Herba Swertiae bimaculatae lactone compounds, gained compound amount is few and the production cycle is long, is difficult to industrialization and produces.Therefore, a kind of method providing industrialization easy and simple to handle, with low cost to prepare Herba Swertiae bimaculatae lactone is significant for applying of Herba Swertiae bimaculatae lactone.
Summary of the invention
The first object of the present invention is to provide a kind of swertiamarin thermal transition product; Second object is the preparation method providing described swertiamarin thermal transition product; 3rd object is the preparation providing described swertiamarin thermal transition product; 4th object is the application providing described swertiamarin thermal transition product.
The first object of the present invention is achieved in that with swertiamarin to be that raw material prepares through thermal conversion, wash-out separation and purification, and described swertiamarin thermal transition product contains the Herba Swertiae bimaculatae lactone composition of weight percent more than 60%.
The second object of the present invention is achieved in that and comprises the following steps:
A, get raw material swertiamarin, add the water of 1 ~ 20 times of weight, obtain conversion fluid in more than 80 DEG C backflow 5 ~ 7h to swertiamarin completely dissolve;
B, by conversion fluid cool, filter obtain filtrate and filter residue, 80 ~ 120 object silica gel mixed samples of filter residue weight ratio 0.1 ~ 2 times are added in filter residue, upper silicagel column, gradient elution is carried out with the sherwood oil-acetone soln of volume proportion 15:1 ~ 3:1, the chloroform-methanol of volume proportion 20:1 ~ 0:1 is used to carry out gradient elution again, elutriant is collected in TLC monitoring, and concentrating under reduced pressure obtains target compound.
The third object of the present invention is achieved in that adding the auxiliary material pharmaceutically accepted in described swertiamarin thermal transition product is prepared into tablet, capsule, granule, injection, lipomul, micro-capsule or dripping pill.
The fourth object of the present invention is achieved in that described swertiamarin thermal transition product is preparing the application in the relevant epidemic disease medicine of preventing/treating liver injury.
Beneficial effect of the present invention:
1, a large amount of Herba Swertiae bimaculatae lactones is contained in the swertiamarin thermal transition product that the present invention obtains, Herba Swertiae bimaculatae lactone composition content in plant materials is very humble, and it is with high costs therefrom to carry out extraction and isolation, is worth without commercial application, and its complex structure, also cannot carry out chemosynthesis acquisition at present.The present invention, by extensively and the swertiamarin be present in a large number in various plants carries out thermal conversion, can obtain such material in a large number, for the further further investigation of this constituents and industrialization breach technical bottleneck.
2, the method for the invention is easy and simple to handle, cost is low, is easy to suitability for industrialized production.
3, the swertiamarin thermal transition product obtained in the present invention has and protects the liver anti-inflammatory activity, and its activity is better than swertiamarin itself, and it may be used for hepatic.
4, swertiamarin thermal transition product has anti-hepatitis B virus activities, can be used for hepatitis B virus resisting medicine.
Embodiment
Below in conjunction with embodiment, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or replacement, all belong to protection scope of the present invention.
Swertiamarin thermal transition product of the present invention, be that raw material prepares through thermal conversion, wash-out separation and purification with swertiamarin, described swertiamarin thermal transition product contains the Herba Swertiae bimaculatae lactone composition of weight percent more than 60%.
Containing Herba Swertiae bimaculatae lactone A ~ M(swerilactone A ~ M in described Herba Swertiae bimaculatae lactone composition) in more than 3 kinds or 3 kinds compositions.
Erthrocentaurin also containing weight percent 0.1 ~ 10% in described swertiamarin thermal transition product.
The weight percent of described erthrocentaurin is 1 ~ 6%.
The preparation method of swertiamarin thermal transition product of the present invention, comprises the following steps:
A, get raw material swertiamarin, add the water of 1 ~ 20 times of weight, obtain conversion fluid in more than 80 DEG C backflow 5 ~ 7h to swertiamarin completely dissolve;
B, by conversion fluid cool, filter obtain filtrate and filter residue, 80 ~ 120 object silica gel mixed samples of filter residue weight ratio 0.1 ~ 2 times are added in filter residue, upper silicagel column, gradient elution is carried out with the sherwood oil-acetone soln of volume proportion 15:1 ~ 3:1, the chloroform-methanol of volume proportion 20:1 ~ 0:1 is used to carry out gradient elution again, elutriant is collected in TLC monitoring, and concentrating under reduced pressure obtains target compound.
The temperature of the backflow described in step A is 90 ~ 100 DEG C.
The monitoring of the swertiamarin completely dissolve described in step A adopts TLC monitoring.
Preparation of the present invention in described swertiamarin thermal transition product, adds the auxiliary material pharmaceutically accepted be prepared into tablet, capsule, granule, injection, lipomul, micro-capsule or dripping pill.
Of the present inventionly be applied as described swertiamarin thermal transition product and preparing the application in the relevant epidemic disease medicine of preventing/treating liver injury.
With embodiment, the present invention will be further described below:
Embodiment 1
Get swertiamarin 20kg, add the water of 15 times of weight, be warming up to 95 DEG C and carry out conversion reaction, after testing after swertiamarin completely dissolve, reaction stops, and is cooled to room temperature, filters to obtain filter residue; The silica gel mixed sample of 1.5 times of weight is added in filter residue, silicagel column is loaded after oven dry, first use sherwood oil-acetone (15:1-3:1) gradient elution, chloroform-methanol (20:1-0:1) is used to carry out gradient elution again, collect target component, concentrate, dry to obtain swertiamarin thermal transition product, after testing, Herba Swertiae bimaculatae lactone accounts for 76% of thermal transition product total amount, wherein containing Herba Swertiae bimaculatae lactone G, swerilactone I, swerilactone J, swerilactone K; Erthrocentaurin accounts for 6% of thermal transition product total amount.
Embodiment 2
Get swertiamarin 30kg, add the water of 20 times of weight, be warming up to 100 DEG C and carry out conversion reaction, after testing after swertiamarin completely dissolve, reaction stops, and is cooled to room temperature, filters to obtain filter residue; The silica gel mixed sample of 2 times of weight is added in filter residue, silicagel column is loaded after oven dry, first use sherwood oil-acetone (15:1-3:1) gradient elution, chloroform-methanol (20:1-0:1) is used to carry out gradient elution again, collect target component, concentrate, dry to obtain swertiamarin thermal transition product, after testing, Herba Swertiae bimaculatae lactone accounts for 80% of thermal transition product total amount, wherein containing Herba Swertiae bimaculatae lactone A, Herba Swertiae bimaculatae lactone C, swerilactone J, swerilactone K, Herba Swertiae bimaculatae lactone M; Erthrocentaurin accounts for 4% of thermal transition product total amount.
Embodiment 3
Get swertiamarin 10 kg, add the water of 5 times of weight, be warming up to 100 DEG C and carry out conversion reaction, after testing after swertiamarin completely dissolve, reaction stops, and is cooled to room temperature, filters to obtain filter residue; The silica gel mixed sample of 1 times of weight is added in filter residue, silicagel column is loaded after oven dry, first use sherwood oil-acetone (15:1-3:1) gradient elution, chloroform-methanol (20:1-0:1) is used to carry out gradient elution again, collect target component, concentrate, dry to obtain swertiamarin thermal transition product, after testing, Herba Swertiae bimaculatae lactone accounts for 79% of thermal transition product total amount, wherein containing Herba Swertiae bimaculatae lactone A, Herba Swertiae bimaculatae lactone D, swerilactone J, swerilactone K, Herba Swertiae bimaculatae lactone M; Erthrocentaurin accounts for 6% of thermal transition product total amount.
Embodiment 4
Get swertiamarin 15 kg, add the water of 1 times of weight, be warming up to 100 DEG C and carry out conversion reaction, after testing after swertiamarin completely dissolve, reaction stops, and is cooled to room temperature, filters to obtain filter residue; The silica gel mixed sample of 1.5 times of weight is added in filter residue, silicagel column is loaded after oven dry, first use sherwood oil-acetone (15:1-3:1) gradient elution, chloroform-methanol (20:1-0:1) is used to carry out gradient elution again, collect target component, concentrate, dry to obtain swertiamarin thermal transition product, after testing, Herba Swertiae bimaculatae lactone accounts for 76% of thermal transition product total amount, wherein containing Herba Swertiae bimaculatae lactone B, swerilactone J, swerilactone K, Herba Swertiae bimaculatae lactone M; Erthrocentaurin accounts for 5% of thermal transition product total amount.
Embodiment 5
Get swertiamarin 25 kg, add the water of 20 times of weight, be warming up to 90 DEG C and carry out conversion reaction, after testing after swertiamarin completely dissolve, reaction stops, and is cooled to room temperature, filters to obtain filter residue; The silica gel mixed sample of 2 times of weight is added in filter residue, silicagel column is loaded after oven dry, first use sherwood oil-acetone (15:1-3:1) gradient elution, chloroform-methanol (20:1-0:1) is used to carry out gradient elution again, collect target component, concentrate, dry to obtain swertiamarin thermal transition product, after testing, Herba Swertiae bimaculatae lactone accounts for 76% of thermal transition product total amount, wherein containing Herba Swertiae bimaculatae lactone C, swerilactone J, swerilactone K, Herba Swertiae bimaculatae lactone M; Erthrocentaurin accounts for 6% of thermal transition product total amount.
Embodiment 6
Herba Swertiae bimaculatae lactone compound prepared by Example 1 adds pharmaceutically acceptable auxiliary material and makes tablet.
Embodiment 7
Herba Swertiae bimaculatae lactone compound prepared by Example 2 adds pharmaceutically acceptable auxiliary material and makes capsule.
Embodiment 8
Herba Swertiae bimaculatae lactone compound prepared by Example 3 adds pharmaceutically acceptable auxiliary material and makes granule.
Embodiment 9
Herba Swertiae bimaculatae lactone compound prepared by Example 4 adds pharmaceutically acceptable auxiliary material and makes injection.
Embodiment 10
Herba Swertiae bimaculatae lactone compound prepared by Example 5 adds pharmaceutically acceptable auxiliary material and makes lipomul.
Embodiment 11
Herba Swertiae bimaculatae lactone compound prepared by Example 5 adds pharmaceutically acceptable auxiliary material and makes micro-capsule.
Embodiment 12
Herba Swertiae bimaculatae lactone compound prepared by Example 3 adds pharmaceutically acceptable auxiliary material and makes dripping pill.
Embodiment 13
Test with swertiamarin thermal transition product prepared by embodiment 3, its result is as follows:
One, anti-CCl4 liver injury experiment
Select 18 ~ 22g male mice in kunming 82, be divided into 7 groups at random by body weight: Normal group; Model control group; Bifendate drop pill 200mg/kg group; Swertiamarin 0.52,1.05g/kg group; Swertiamarin thermal transition thing 0.42g, 0.84g/kg group prepared by embodiment 3; Except normal group 10 animals, all the other often organize 12.Each treated animal every day according to dosage gastric infusion once, continuous 7 days.30min after administration on the 6th, except Normal group, the CCl of the equal abdominal injection 0.12% of each animal pattern
4olive oil solution 0.1ml/10g.bw.After modeling, 30min after water 16h, i.e. last administration is can't help in fasting, and eye socket gets blood separation of serum, measures ALT and AST, the results are shown in Table 1.
Swertiamarin thermal transition thing prepared by table 1 embodiment 3 is to CCl
4cause the impact of acute liver
Note: compared with normal group:
△ △ p<0.01; Compared with model group, *
/* P<0.05/0.01
As shown in Table 1, model group animal serum ALT, AST are significantly higher than Normal group, show experiment modeling success; The swertiamarin thermal transition thing group of positive control Biphenylylmethylcarbinol, embodiment 3 preparation all obviously can reduce CCl
4the Serum ALT of induced Acute liver injury mouse and AST; Particularly its effect of swertiamarin conversion product low dose group of embodiment 3 preparation is quite active with Biphenylylmethylcarbinol positive controls, and its high dose group is then significantly higher than positive controls; And the anti-CCl of swertiamarin thermal transition thing
4caused liver injury activity is also significantly higher than swertiamarin itself.
Two, anti-hepatitis B virus activity test
Test philosophy: with HepG2.2.15 cell for hepatitis B poisonous carrier, the swertiamarin thermal transition product measuring embodiment 3 preparation produces the impact of the activity of HbsAg, HBeAg to HBV virus in sample.
Testing method:
Get the recovery of HepG 2.2.15 cell strain, and be resuspended in perfect medium, at 37 DEG C, 5% CO
2cultivate under condition, go down to posterity 1 time every 2d, ensure that experiment cell used is in logarithmic phase.With trypsinase, attached cell HepG 2.2.15 is digested, and be 3 × 10 with substratum by resuspended for cell and dilution
4the cell suspension of/mL, be inoculated in 96 orifice plates by every hole 100 μ L and cultivate, after 24 h, cell grows up to individual layer, and the liquid adding different concns starts to test.Often kind of medicine, with 2.5% dmso solution, is made into mother liquor with substratum; 4 concentration gradients established by often kind of medicine, and each concentration gradient establishes 3 multiple holes, take lamivudine as positive control drug; Every plate establishes the normal cell not adding medicine to make blank.Be positioned over 37 DEG C, 5% CO
2cultivate under condition, after 48h, collect supernatant liquor.Get supernatant liquor, adopt euzymelinked immunosorbent assay (ELISA), with hepatitis B surface antigen and e antigen detection kit, in microplate reader with 630 nm for reference wavelength, 450 nm are that determined wavelength detects, read absorbancy (
a) value, detection of drugs to the restraining effect of emiocytosis HBsAg, HBeAg, medicine to the inhibiting rate of antigen=(
agroups of cells-
aexperimental group)/(
agroups of cells-
ablank group), the drug level that IC50 value is medicine when being 50% to the inhibiting rate of HBsAg or HBeAg.Suck in the cell hole of supernatant and add the serum-free medium of 100 μ L/ holes containing 0.4 g/L MTT, at 37 DEG C, 5% CO
2continue cultivation 4 h under condition, remove supernatant liquor, with 100 μ L/ hole dmso solutions, under 490 nm wavelength, measure it by microplate reader
avalue, detection of drugs to the toxic action of cell, medicine to the destructive rate of cell=(
agroups of cells-
aexperimental group)/(
agroups of cells-
ablank group), medicine half toxic concentration (CC50) is drug level when test holes survivaling cell is control wells cell 50%.Therapeutic index (SI)=CC50/IC50.Be that low toxicity is effective as SI > 2, being poor efficiency high poison during 1 < SI < 2, is nontoxic invalid during SI < 1.
Swertiamarin thermal transition product anti-hepatitis B virus activity prepared by table 2 embodiment 3
As seen from the results in Table 2, the swertiamarin thermal transition product of embodiment 3 preparation is to the IC of HbsAg
50be less than 0.05 mgmL
-1, IC to HBeAg
50be less than 0.07 mgmL
-1, show that swertiamarin thermal transition product prepared by embodiment 3 all has stronger inhibit activities to HbsAg, HBeAg.Result shows that swertiamarin thermal transition product prepared by embodiment 3 can be used for preparing the medicine preventing or treat hepatitis B.
Embodiment 14
The Herba Swertiae bimaculatae lactone compound prepared with embodiment 1,2,4,5 is respectively tested, and test method is identical with embodiment 13, and result all shows that swertiamarin thermal transition product prepared by the present invention all has stronger inhibit activities to HbsAg, HBeAg.Show that swertiamarin thermal transition product prepared by the present invention can be used for preparing the medicine preventing or treat hepatitis B.
Claims (9)
1. a swertiamarin thermal transition product, it is characterized in that being that raw material prepares through thermal conversion, wash-out separation and purification with swertiamarin, described swertiamarin thermal transition product contains the Herba Swertiae bimaculatae lactone composition of weight percent more than 60%.
2. swertiamarin thermal transition product according to claim 1, is characterized in that in described Herba Swertiae bimaculatae lactone composition containing Herba Swertiae bimaculatae lactone A ~ M(swerilactone A ~ M) in more than 3 kinds or 3 kinds compositions.
3. swertiamarin thermal transition product according to claim 1, is characterized in that the erthrocentaurin also containing weight percent 0.1 ~ 10% in described swertiamarin thermal transition product.
4. swertiamarin thermal transition product according to claim 3, is characterized in that the weight percent of described erthrocentaurin is 1 ~ 6%.
5. a preparation method for the arbitrary described swertiamarin thermal transition product of claim 1 ~ 4, is characterized in that comprising the following steps:
A, get raw material swertiamarin, add the water of 1 ~ 20 times of weight, obtain conversion fluid in more than 80 DEG C backflow 5 ~ 7h to swertiamarin completely dissolve;
B, by conversion fluid cool, filter obtain filtrate and filter residue, 80 ~ 120 object silica gel mixed samples of filter residue weight ratio 0.1 ~ 2 times are added in filter residue, upper silicagel column, gradient elution is carried out with the sherwood oil-acetone soln of volume proportion 15:1 ~ 3:1, the chloroform-methanol of volume proportion 20:1 ~ 0:1 is used to carry out gradient elution again, elutriant is collected in TLC monitoring, and concentrating under reduced pressure obtains target compound.
6. preparation method according to claim 5, is characterized in that the temperature of the backflow described in step A is 90 ~ 100 DEG C.
7. preparation method according to claim 5, is characterized in that the monitoring of the swertiamarin completely dissolve described in step A adopts TLC monitoring.
8. a preparation for the arbitrary described swertiamarin thermal transition product of claim 1 ~ 4, it is characterized in that in described swertiamarin thermal transition product, add the auxiliary material pharmaceutically accepted is prepared into tablet, capsule, granule, injection, lipomul, micro-capsule or dripping pill.
9. an application for the arbitrary described swertiamarin thermal transition product of claim 1 ~ 4, is characterized in that described swertiamarin thermal transition product is preparing the application in the relevant epidemic disease medicine of preventing/treating liver injury.
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| CN103265536A (en) * | 2013-05-24 | 2013-08-28 | 南京泽朗医药科技有限公司 | Preparation method of swertisin |
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2014
- 2014-12-30 CN CN201410839888.8A patent/CN104497005A/en active Pending
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| JP2005002056A (en) * | 2003-06-12 | 2005-01-06 | Pola Chem Ind Inc | Dendrite growth promoter of melanocyte, and cosmetic containing the same |
| CN102532156A (en) * | 2010-12-15 | 2012-07-04 | 中国科学院昆明植物研究所 | Swerilactones H-K, 1-4 and medicinal composition and application thereof |
| CN103265536A (en) * | 2013-05-24 | 2013-08-28 | 南京泽朗医药科技有限公司 | Preparation method of swertisin |
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| CHANG-AN GENG ET AL.: ""Anti-Hepatitis B Virus Active Lactones from the Traditional Chinese Herb: Swertia mileensis"", 《CHEM. EUR. J.》 * |
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Application publication date: 20150408 |