CN110483596A - A kind of compound Swertiaside of anti-hepatitis virus - Google Patents
A kind of compound Swertiaside of anti-hepatitis virus Download PDFInfo
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- CN110483596A CN110483596A CN201910851470.1A CN201910851470A CN110483596A CN 110483596 A CN110483596 A CN 110483596A CN 201910851470 A CN201910851470 A CN 201910851470A CN 110483596 A CN110483596 A CN 110483596A
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- swertiaside
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- hepatitis virus
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- ethanol water
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
Abstract
The present invention relates to a kind of compound Swertiaside of anti-hepatitis virus, mountain ketoside class of the compound Swertiaside in Tibetan medicine material mussot swertia herb, molecular formula C25H28O15, chemical structural formula is as follows:.The invention also discloses the Preparation method and uses of the compound simultaneously.Gained compound of the invention is the guiding drug for treating hepatitis B and early liver cancer, and the exploitation of product will bring new hope for patient.
Description
Technical field
The present invention relates to pharmaceutical technology field more particularly to a kind of compound Swertiaside of anti-hepatitis virus.
Background technique
Throughout our country in crowd, hepatitis type B virus (hepatitis B viNs, HBV) infection rate be 42.4% ~
80.7%, hepatitis b virus carrier (AsC) can be more than 1.2 hundred million people, account for 1/3 or more of hundred million people of whole world AsC3.5.Second
It is more than 3,000 ten thousand people that type hepatitis, which shows disease patient, and the illness rate of chronic hepatitis B (CHB) is 0.1% ~ 1%.50% ~ 70% in AsC
Virus replication is active, is chronic hepatitis B (CHB).5 years follow-up investigations show that patient's CHB cirrhosis incidence is 2% ~ 20%, generation
Repaying property cirrhosis progress is 20% ~ 23% at Decompensational cirrhosis, and develop into liver cancer accounts for 6% ~ 15%.It calculates according to investigations, China
Patient CHB in, about 25% ~ 40% will eventually die of cirrhosis or merge liver cancer.AsC ultimately succumbs to the risk of related liver disease,
Male is 50%, and women 15%.Virus hepatitis brings great harm to people's health, and country, which is often only, is directly used in virus
The payment for medical care of property hepatitis is as high as 300 ~ 50,000,000,000 yuan！
Mussot swertia herb (Swertia mussotii Franch.) it is Gentianaceae Swertia plant, originate in China Qinghai-Tibet height
Original, traditional Tibetan medicine is civil for treating the herbal medicine of hepatitis, but there is not been reported for the research of its anti-hepatitis virus.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of compound Swertiaside of anti-hepatitis virus.
Another technical problem to be solved by this invention is to provide the compound Swertiaside's of the anti-hepatitis virus
Preparation method.
To solve the above problems, a kind of compound Swertiaside of anti-hepatitis virus of the present invention, feature exist
In: mountain ketoside class of the compound Swertiaside in Tibetan medicine material mussot swertia herb, molecular formula C25H28O15, change
It is as follows to learn structural formula:
A kind of preparation method of the compound Swertiaside of anti-hepatitis virus as described above, comprising the following steps:
(1) after mussot swertia herb herb being broken into pieces, 10 ~ 14 h, then heated reflux are impregnated with the ethyl alcohol that volumetric concentration is 95%
It extracts, obtains extracting solution；
(2) the extracting solution is centrifuged after refrigerating 48h, obtains supernatant, which obtains medicinal extract through ethyl alcohol is recovered under reduced pressure；
(3) the medicinal extract is scattered in the water of 1 ~ 5 times of its quality, obtains mixed liquor, and the mixed liquor is successively with the stone isometric with it
Oily ether, ethyl acetate, extracting n-butyl alcohol are multiple, respectively obtain four partial extraction objects: petroleum ether moiety, ethyl acetate portion,
N-butanol fraction, water section；
On the water section macroporous absorbent resin slightly successively use from rear water, volumetric concentration for 5% ethanol water,
20% ethanol water, 50% ethanol water, 95% ethanol water carry out gradient elution, collect 50% ethanol water and elute liquid；
(5) after the 50% ethanol water elution liquid is separated using preparative high-performance liquid chromatographic, Swertiaside crude product is obtained,
The Swertiaside crude product is crystallized after the methanol aqueous solution dissolution that volumetric concentration is 70 ~ 90%, is filtered up to pure compounds.
The step (1) in heating and refluxing extraction condition refer to that temperature is 60 DEG C ~ 80 DEG C, extraction time is 2 ~ 3 times, every time 2
Hour.
(2) middle centrifugal condition refers to that rate is 3000r/min ~ 5000r/min to the step, and the time is 5min ~ 20min.
The step (2) in be recovered under reduced pressure condition refer to temperature be 30 DEG C ~ 50 DEG C, the time be 0.5h ~ 2.0h.
(3) middle extraction conditions refers to that temperature is room temperature to the step, and the time is 0.5h ~ 5.0h.
(4) middle macroporous absorbent resin refers to low pole macroreticular resin to the step.
The step (5) in preparative high-performance liquid chromatographic mobile phase refer to that volumetric concentration is 30 ~ 80% methanol aqueous solution
Or the acetonitrile solution that volumetric concentration is 20 ~ 70%.
A kind of compound Swertiaside of anti-hepatitis virus as described above is in preparation hepatitis B and early liver cancer medicine
Application in object, it is characterised in that: compound Swertiaside be equipped with medicinal stone and it is pharmacological or physiological on can connect
The carrier received is prepared into any dosage form in pharmacy with conventional preparation process.
Compared with the prior art, the present invention has the following advantages:
1, the present invention is the anti-hepatitis B compound Swertiaside separated from the Tibetan medicine material mussot swertia herb for being grown in Tibet,
The Swertiaside be yellow needles (95% ethyl alcohol), 232.2 DEG C of fusing point, [α]D 20: -51.6 (pyridines), λMax MeOH
(nm): 229,265,305.After multiple spectrum is analyzed, it is determined that the compound is mountain ketoside.
Molecular formula C25H28O15；1H(100Hz, DMSO-d6),13C(100Hz, DMSO-d6) nuclear magnetic resonance modal data is shown in Table 1, table 2.
1 Swertiade's of table1H NMR data (ppm)
2 Swertiade's of table13C NMR data (ppm)
2, carry out that duck virion is inside and outside has carried out anti-hepatitis virus experiment to Swertiaside of the present invention, it was demonstrated that compound pair
The duplication of HBV DNA significantly inhibits, IC50Value is between 0.01 ~ 0.13 mM；HBsAg and HBeAg are divided
Secreting also has good inhibiting effect, IC50Value is respectively 0.77,0.62,0.35,0.04 mM of > 0.98,0.21 mM and <.
Experimental result is shown in Table 3 ~ 6 and Fig. 1:
3. compound of table and Lamivudine are in 2215 cell culture to cytotoxicity
4. compound of table and Lamivudine are in 2215 cell culture to the inhibiting effect (%) of HBsAg and HBeAg
The effect of 5. compound of table and Lamivudine in 2215 cell culture to HBV-DNA in supernatant
The effect of 6. compound of table and Lamivudine in 2215 cell culture to intracellular HBV-DNA
In conclusion the compounds of this invention is secreted to hepatitis type B virus HBsAg and HBeAg and HBV-DNA inhibits with good
Good effect has inhibiting effect to the human liver cancer cell 2.2.15 cell of hepatitis type B virus transfection, and has significant and very aobvious
Write the effect for inhibiting the clear DHBV-DNA of duck blood, the treatment especially suitable for hepatitis B and early liver cancer.
3, present invention gained compound is the guiding drug for treating hepatitis B and early liver cancer, and the exploitation of product will be
Patient brings new hope.
Detailed description of the invention
Specific embodiments of the present invention will be described in further detail with reference to the accompanying drawing.
Fig. 1 is oral the compounds of this invention in duck hepatitis B virus infection duck interior therapeutic group and virus-infected controls group
The comparison of the horizontal inhibiting rate of the clear DHBV-DNA of duck blood.
Specific embodiment
A kind of compound Swertiaside of anti-hepatitis virus, compound Swertiaside derive from Tibetan medicine material Chuan Xi
Mountain ketoside class in Swertia patens, molecular formula C25H28O15, chemical structural formula is as follows:
The preparation method of the compound Swertiaside of the anti-hepatitis virus of embodiment 1 a kind of, comprising the following steps:
(1) after mussot swertia herb herb being broken into pieces, 10 h are impregnated with the ethyl alcohol that volumetric concentration is 95%, are then 60 DEG C in temperature
Under the conditions of heating and refluxing extraction 2 times, 2 hours every time, merging obtain extracting solution.
(2) extracting solution is centrifuged 20min after refrigerating 48h with the rate of 3000r/min, obtains supernatant, the supernatant is through 30
Ethyl alcohol DEG C is recovered under reduced pressure, after 2.0h medicinal extract.
(3) medicinal extract is scattered in the water of 1 times of its quality, obtains mixed liquor, successively with isometric with it under the mixed liquor room temperature
Petroleum ether, ethyl acetate, extracting n-butyl alcohol it is multiple, each 0.5h respectively obtains four partial extraction objects: petroleum ether moiety,
Ethyl acetate portion, n-butanol fraction, water section.
(4) low pole macroporous absorbent resin carries out slightly successively using water, volumetric concentration for 5% ethanol water from rear on water section
Solution, 20% ethanol water, 50% ethanol water, 95% ethanol water carry out gradient elution, collect 50% ethanol water
Eluent.
(5) after 50% ethanol water elution liquid is separated using preparative high-performance liquid chromatographic, it is thick that Swertiaside is obtained
Product, the Swertiaside crude product are crystallized after the methanol aqueous solution dissolution that volumetric concentration is 70%, are filtered up to pure compounds.
Wherein: mobile phase refers to that volumetric concentration is 30% methanol aqueous solution in preparative high-performance liquid chromatographic.
The preparation method of the compound Swertiaside of the anti-hepatitis virus of embodiment 2 a kind of, comprising the following steps:
(1) after mussot swertia herb herb being broken into pieces, 14 h are impregnated with the ethyl alcohol that volumetric concentration is 95%, are then 80 DEG C in temperature
Under the conditions of heating and refluxing extraction 3 times, 2 hours every time, merging obtain extracting solution.
(2) extracting solution is centrifuged 5min after refrigerating 48h with the rate of 5000r/min, obtains supernatant, the supernatant is through 50
Ethyl alcohol DEG C is recovered under reduced pressure, after 0.5h medicinal extract.
(3) medicinal extract is scattered in the water of 5 times of its quality, obtains mixed liquor, successively with isometric with it under the mixed liquor room temperature
Petroleum ether, ethyl acetate, extracting n-butyl alcohol it is multiple, each 5.0h respectively obtains four partial extraction objects: petroleum ether moiety,
Ethyl acetate portion, n-butanol fraction, water section.
(4) low pole macroporous absorbent resin carries out slightly successively using water, volumetric concentration for 5% ethanol water from rear on water section
Solution, 20% ethanol water, 50% ethanol water, 95% ethanol water carry out gradient elution, collect 50% ethanol water
Eluent.
(5) after 50% ethanol water elution liquid is separated using preparative high-performance liquid chromatographic, it is thick that Swertiaside is obtained
Product, the Swertiaside crude product are crystallized after the methanol aqueous solution dissolution that volumetric concentration is 90%, are filtered up to pure compounds.
Wherein: mobile phase refers to that volumetric concentration is 80% methanol aqueous solution in preparative high-performance liquid chromatographic.
The preparation method of the compound Swertiaside of the anti-hepatitis virus of embodiment 3 a kind of, comprising the following steps:
(1) after mussot swertia herb herb being broken into pieces, 12 h are impregnated with the ethyl alcohol that volumetric concentration is 95%, are then 70 DEG C in temperature
Under the conditions of heating and refluxing extraction 2 times, 2 hours every time, merging obtain extracting solution.
(2) extracting solution is centrifuged 15min after refrigerating 48h with the rate of 4000r/min, obtains supernatant, the supernatant is through 40
Ethyl alcohol DEG C is recovered under reduced pressure, after 1.0h medicinal extract.
(3) medicinal extract is scattered in the water of 3 times of its quality, obtains mixed liquor, successively with isometric with it under the mixed liquor room temperature
Petroleum ether, ethyl acetate, extracting n-butyl alcohol it is multiple, each 2.5h respectively obtains four partial extraction objects: petroleum ether moiety,
Ethyl acetate portion, n-butanol fraction, water section.
(4) low pole macroporous absorbent resin carries out slightly successively using water, volumetric concentration for 5% ethanol water from rear on water section
Solution, 20% ethanol water, 50% ethanol water, 95% ethanol water carry out gradient elution, collect 50% ethanol water
Eluent.
(5) after 50% ethanol water elution liquid is separated using preparative high-performance liquid chromatographic, it is thick that Swertiaside is obtained
Product, the Swertiaside crude product are crystallized after the methanol aqueous solution dissolution that volumetric concentration is 80%, are filtered up to pure compounds.
Wherein: mobile phase refers to that volumetric concentration is 60% methanol aqueous solution in preparative high-performance liquid chromatographic.
The preparation method of the compound Swertiaside of the anti-hepatitis virus of embodiment 4 a kind of, comprising the following steps:
(1) after mussot swertia herb herb being broken into pieces, 11 h are impregnated with the ethyl alcohol that volumetric concentration is 95%, are then 65 DEG C in temperature
Under the conditions of heating and refluxing extraction 2 times, 2 hours every time, merging obtain extracting solution.
(2) extracting solution is centrifuged 18min after refrigerating 48h with the rate of 3500r/min, obtains supernatant, the supernatant is through 35
Ethyl alcohol DEG C is recovered under reduced pressure, after 1.5h medicinal extract.
(3) medicinal extract is scattered in the water of 2 times of its quality, obtains mixed liquor, successively with isometric with it under the mixed liquor room temperature
Petroleum ether, ethyl acetate, extracting n-butyl alcohol it is multiple, each 1.0h respectively obtains four partial extraction objects: petroleum ether moiety,
Ethyl acetate portion, n-butanol fraction, water section.
(4) low pole macroporous absorbent resin carries out slightly successively using water, volumetric concentration for 5% ethanol water from rear on water section
Solution, 20% ethanol water, 50% ethanol water, 95% ethanol water carry out gradient elution, collect 50% ethanol water
Eluent.
(5) after 50% ethanol water elution liquid is separated using preparative high-performance liquid chromatographic, it is thick that Swertiaside is obtained
Product, the Swertiaside crude product are crystallized after the methanol aqueous solution dissolution that volumetric concentration is 75%, are filtered up to pure compounds.
Wherein: mobile phase refers to that volumetric concentration is 20% acetonitrile solution in preparative high-performance liquid chromatographic.
The preparation method of the compound Swertiaside of the anti-hepatitis virus of embodiment 5 a kind of, comprising the following steps:
(1) after mussot swertia herb herb being broken into pieces, 13 h are impregnated with the ethyl alcohol that volumetric concentration is 95%, are then 75 DEG C in temperature
Under the conditions of heating and refluxing extraction 2 times, 2 hours every time, merging obtain extracting solution.
(2) extracting solution is centrifuged 10min after refrigerating 48h with the rate of 4500r/min, obtains supernatant, the supernatant is through 45
Ethyl alcohol DEG C is recovered under reduced pressure, after 0.8h medicinal extract.
(3) medicinal extract is scattered in the water of 4 times of its quality, obtains mixed liquor, successively with isometric with it under the mixed liquor room temperature
Petroleum ether, ethyl acetate, extracting n-butyl alcohol it is multiple, each 3.0h respectively obtains four partial extraction objects: petroleum ether moiety,
Ethyl acetate portion, n-butanol fraction, water section.
(4) low pole macroporous absorbent resin carries out slightly successively using water, volumetric concentration for 5% ethanol water from rear on water section
Solution, 20% ethanol water, 50% ethanol water, 95% ethanol water carry out gradient elution, collect 50% ethanol water
Eluent.
(5) after 50% ethanol water elution liquid is separated using preparative high-performance liquid chromatographic, it is thick that Swertiaside is obtained
Product, the Swertiaside crude product are crystallized after the methanol aqueous solution dissolution that volumetric concentration is 85%, are filtered up to pure compounds.
Wherein: mobile phase refers to that volumetric concentration is 70% acetonitrile solution in preparative high-performance liquid chromatographic.
The preparation method of the compound Swertiaside of the anti-hepatitis virus of embodiment 6 a kind of, comprising the following steps:
(1) after mussot swertia herb herb being broken into pieces, 10 h are impregnated with the ethyl alcohol that volumetric concentration is 95%, are then 60 DEG C in temperature
Under the conditions of heating and refluxing extraction 2 times, 2 hours every time, merging obtain extracting solution.
(2) extracting solution is centrifuged 20min after refrigerating 48h with the rate of 3000r/min, obtains supernatant, the supernatant is through 30
Ethyl alcohol DEG C is recovered under reduced pressure, after 2.0h medicinal extract.
(3) medicinal extract is scattered in the water of 3 times of its quality, obtains mixed liquor, successively with isometric with it under the mixed liquor room temperature
Petroleum ether, ethyl acetate, extracting n-butyl alcohol it is multiple, each 4.0h respectively obtains four partial extraction objects: petroleum ether moiety,
Ethyl acetate portion, n-butanol fraction, water section.
(4) low pole macroporous absorbent resin carries out slightly successively using water, volumetric concentration for 5% ethanol water from rear on water section
Solution, 20% ethanol water, 50% ethanol water, 95% ethanol water carry out gradient elution, collect 50% ethanol water
Eluent.
(5) after 50% ethanol water elution liquid is separated using preparative high-performance liquid chromatographic, it is thick that Swertiaside is obtained
Product, the Swertiaside crude product are crystallized after the methanol aqueous solution dissolution that volumetric concentration is 70%, are filtered up to pure compounds.
Wherein: mobile phase refers to that volumetric concentration is 45% acetonitrile solution in preparative high-performance liquid chromatographic.
The compound Swertiaside of the resulting anti-hepatitis virus of above-described embodiment 1 ~ 6 is in preparation hepatitis B and early stage
In liver-cancer medicine application refer to: compound Swertiaside be equipped with medicinal stone and it is pharmacological or physiological on can connect
The carrier received is prepared into any dosage form in pharmacy with conventional preparation process.
Claims (9)
1. a kind of compound Swertiaside of anti-hepatitis virus, it is characterised in that: compound Swertiaside is derived from
Mountain ketoside class in Tibetan medicine material mussot swertia herb, molecular formula C25H28O15, chemical structural formula is as follows:
。
2. a kind of preparation method of the compound Swertiaside of anti-hepatitis virus as described in claim 1, including following step
It is rapid:
(1) after mussot swertia herb herb being broken into pieces, 10 ~ 14 h, then heated reflux are impregnated with the ethyl alcohol that volumetric concentration is 95%
It extracts, obtains extracting solution；
(2) the extracting solution is centrifuged after refrigerating 48h, obtains supernatant, which obtains medicinal extract through ethyl alcohol is recovered under reduced pressure；
(3) the medicinal extract is scattered in the water of 1 ~ 5 times of its quality, obtains mixed liquor, and the mixed liquor is successively with the stone isometric with it
Oily ether, ethyl acetate, extracting n-butyl alcohol are multiple, respectively obtain four partial extraction objects: petroleum ether moiety, ethyl acetate portion,
N-butanol fraction, water section；
On the water section macroporous absorbent resin slightly successively use from rear water, volumetric concentration for 5% ethanol water,
20% ethanol water, 50% ethanol water, 95% ethanol water carry out gradient elution, collect the elution of 50% ethanol water
Liquid；
(5) after the 50% ethanol water elution liquid is separated using preparative high-performance liquid chromatographic, it is thick that Swertiaside is obtained
Product, the Swertiaside crude product through volumetric concentration be 70 ~ 90% methanol aqueous solution dissolution after crystallize, filter up to compound it is pure
Product.
3. a kind of preparation method of the compound Swertiaside of anti-hepatitis virus as claimed in claim 2, feature exist
In: (1) middle heating and refluxing extraction condition refers to that temperature is 60 DEG C ~ 80 DEG C to the step, and extraction time is 2 ~ 3 times, every time 2 hours.
4. a kind of preparation method of the compound Swertiaside of anti-hepatitis virus as claimed in claim 2, feature exist
In: (2) middle centrifugal condition refers to that rate is 3000r/min ~ 5000r/min to the step, and the time is 5min ~ 20min.
5. a kind of preparation method of the compound Swertiaside of anti-hepatitis virus as claimed in claim 2, feature exist
In: the step (2) in condition be recovered under reduced pressure refer to that temperature is 30 DEG C ~ 50 DEG C, the time is 0.5h ~ 2.0h.
6. a kind of preparation method of the compound Swertiaside of anti-hepatitis virus as claimed in claim 2, feature exist
In: (3) middle extraction conditions refers to that temperature is room temperature to the step, and the time is 0.5h ~ 5.0h.
7. a kind of preparation method of the compound Swertiaside of anti-hepatitis virus as claimed in claim 2, feature exist
In: (4) middle macroporous absorbent resin refers to low pole macroreticular resin to the step.
8. a kind of preparation method of the compound Swertiaside of anti-hepatitis virus as claimed in claim 2, feature exist
In: the step (5) in preparative high-performance liquid chromatographic mobile phase refer to methanol aqueous solution or volume that volumetric concentration is 30 ~ 80%
The acetonitrile solution that concentration is 20 ~ 70%.
9. a kind of compound Swertiaside of anti-hepatitis virus as described in claim 1 is in preparation hepatitis B and early stage
Application in liver-cancer medicine, it is characterised in that: compound Swertiaside is equipped with medicinal stone and pharmacological or physiological
Upper acceptable carrier is prepared into any dosage form in pharmacy with conventional preparation process.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0213809A2 (en) * | 1985-08-12 | 1987-03-11 | Kabushiki Kaisha Vitamin Kenkyusyo | Extract of swertia japonica makino and method of obtaining the same |
| CN104370871A (en) * | 2013-08-12 | 2015-02-25 | 北京大学 | Xanthine separated from swertia punicea and application thereof in inhibiting hepatitis B virus |
-
2019
- 2019-09-10 CN CN201910851470.1A patent/CN110483596A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0213809A2 (en) * | 1985-08-12 | 1987-03-11 | Kabushiki Kaisha Vitamin Kenkyusyo | Extract of swertia japonica makino and method of obtaining the same |
| CN104370871A (en) * | 2013-08-12 | 2015-02-25 | 北京大学 | Xanthine separated from swertia punicea and application thereof in inhibiting hepatitis B virus |
Non-Patent Citations (3)
| Title |
|---|
| 于德泉 等: "《分析化学手册》", 31 October 1999, 化学工业出版社 * |
| 田峦鸢等: "紫红獐牙菜醋酸乙酯部位体外抗乙型肝炎病毒作用的研究", 《湖北中医学院学报》 * |
| 陈佩东 主编: "《中药化学》", 31 January 2012, 中国医药科技出版社 * |
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Application publication date: 20191122 |