CN111718360A - Mixed-source terpenoid and preparation method and application thereof - Google Patents
Mixed-source terpenoid and preparation method and application thereof Download PDFInfo
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- CN111718360A CN111718360A CN201910224711.XA CN201910224711A CN111718360A CN 111718360 A CN111718360 A CN 111718360A CN 201910224711 A CN201910224711 A CN 201910224711A CN 111718360 A CN111718360 A CN 111718360A
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- 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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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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Abstract
The invention relates to a mixed source terpenoid (-) -Hyperterpnoid B extracted and separated from Chinese yellow incense (Hypericum paniculatum L.) for the first time, a preparation method and application thereof. The biological activity test shows that: the compound has obvious inhibition activity on the generation of primary mouse abdominal cavity macrophage inflammatory factor NO induced by LPS, shows obvious anti-inflammatory effect and can be used for preparing anti-inflammatory drugs.
Description
Technical Field
The invention relates to the technical field of medicines. Relates to a mixed source terpenoid natural drug (-) -Hyperterpinenoid B with anti-inflammatory activity extracted and separated from the overground part of Chinese yellow croaker (Hypericum paniculatum L.), a preparation method thereof and application thereof in anti-inflammatory treatment.
Background
The herba Cymbopogonis Citrari is a plant of Hypericum of Guttiferae, and has another name: transplanting flowers, yellow-yellow in the road. Is distributed in Guizhou, Yunnan and other places in China. The yellow flower fragrance is bitter in taste and cold in nature; has the effects of clearing heat, promoting diuresis, removing toxic substances and removing blood stasis. Can be used for treating jaundice due to damp-heat pathogen, diarrhea, dysentery, traumatic injury, and arthralgia and myalgia.
Disclosure of Invention
The invention aims to solve the technical problem of providing a mixed source terpenoid compound (-) -Hyperterpnoid B extracted and separated from yellow incense for the first time and pharmaceutically acceptable salts thereof, a preparation method and application thereof.
In order to solve the technical problem, the invention provides the following technical scheme:
the first aspect of the technical scheme of the invention provides a mixed source terpenoid (-) -hyperterpenoid B and pharmaceutically acceptable salts thereof, wherein the structure of the compound is as follows:
the second aspect of the technical scheme of the invention provides a preparation method of a mixed source terpenoid (-) -hyperterpenoid B, which is separated from the overground part of the yellow croaker and comprises the following specific steps:
extraction: extracting the ground aerial parts of the hemerocallis citrina baroni with ethanol, and concentrating the obtained extract to obtain a crude extract; dissolving the crude extract in water, suspending uniformly, extracting with petroleum ether, and concentrating the obtained extract to obtain petroleum ether extract.
Separation: performing silica gel column chromatography on the petroleum ether extract, performing gradient elution by using petroleum ether/ethyl acetate, and performing color development according to TLC (thin layer chromatography) and combining similar fractions to obtain 12 components Fr.1-12; wherein the component Fr.3 is the volume ratio of petroleum ether/ethyl acetate of 20: 1, further performing silica gel column chromatography on the eluted part, wherein the volume ratio of petroleum ether/acetone is 4: elution was performed at 1 isocratic and similar fractions were combined according to TLC visualization to give 6 fractions A, B, C, D, E, F. And the component E is subjected to silica gel column chromatography and eluted by petroleum ether/ethyl acetate gradient, wherein the volume ratio of the petroleum ether to the ethyl acetate is 2: 1 elution fraction E5 was subjected to preparative HPLC with a methanol/water volume ratio of 85: 15 to obtain the compound (-) -hyperterpenoid B.
In the above preparation method, in the extraction step, the ethanol used is 95% ethanol.
In the above preparation method, in the extraction step, the extraction is performed by heating reflux extraction.
In the preparation method, in the separation step, the concentration of the first petroleum ether/ethyl acetate gradient elution is sequentially 1: 0,20: 1,9: 1,4: 1,1: 1,0: 1.
in the preparation method, in the separation step, the concentration of the second petroleum ether/ethyl acetate gradient elution is 1: 0,9: 1,4: 1,2: 1,0: 1.
in the above preparation method, in the separation step, the chromatographic column packing of the preparative HPLC is reverse-phase octadecyl bonded silica gel.
According to a third aspect of the technical scheme, the invention provides a pharmaceutical composition, which is characterized by containing the mixed source terpenoid and the pharmaceutically acceptable salt thereof and the pharmaceutically acceptable salt or additive thereof in claim 1.
The pharmaceutical composition may be prepared according to methods well known in the art. The compounds of the invention may be formulated into any dosage form suitable for human or animal use by combining them with one or more pharmaceutically acceptable solid or liquid excipients and/or adjuvants. The compounds of the present invention are generally present in the pharmaceutical compositions in an amount of from 0.1 to 95% by weight.
The compounds of the present invention or pharmaceutical compositions containing them may be administered in unit dosage form by enteral or parenteral routes, such as oral, intravenous, intramuscular, subcutaneous, nasal, oromucosal, ophthalmic, pulmonary and respiratory, dermal, vaginal, rectal, and the like.
The dosage form for administration may be a liquid dosage form, a solid dosage form, or a semi-solid dosage form. The liquid dosage forms can be solution (including true solution and colloidal solution), emulsion (including o/w type, w/o type and multiple emulsion), suspension, injection (including water injection, powder injection and infusion), eye drop, nose drop, lotion, liniment, etc.; the solid dosage form can be tablet (including common tablet, enteric coated tablet, buccal tablet, dispersible tablet, chewable tablet, effervescent tablet, orally disintegrating tablet), capsule (including hard capsule, soft capsule, and enteric coated capsule), granule, powder, pellet, dripping pill, suppository, pellicle, patch, aerosol (powder), spray, etc.; semisolid dosage forms can be ointments, gels, pastes, and the like.
The compound can be prepared into common preparations, sustained release preparations, controlled release preparations, targeting preparations and various particle drug delivery systems.
For tableting the compound of the present invention, a wide variety of excipients known in the art may be used, including diluents, binders, wetting agents, disintegrants, lubricants, and solubilizers. The diluent can be starch, dextrin, sucrose, glucose, lactose, mannitol, sorbitol, xylitol, microcrystalline cellulose, calcium sulfate, calcium hydrogen phosphate, calcium carbonate, etc.; the humectant can be water, ethanol, isopropanol, etc.; the binder can be starch slurry, dextrin, syrup, Mel, glucose solution, microcrystalline cellulose, acacia slurry, gelatin slurry, sodium carboxymethylcellulose, methylcellulose, hydroxypropyl methylcellulose, ethyl cellulose, acrylic resin, carbomer, polyvinylpyrrolidone, polyethylene glycol, etc.; the disintegrant may be dry starch, microcrystalline cellulose, low-substituted hydroxypropyl cellulose, crosslinked polyvinylpyrrolidone, crosslinked sodium carboxymethylcellulose, sodium carboxymethyl starch, sodium bicarbonate and citric acid, polyoxyethylene sorbitol fatty acid ester, sodium dodecyl sulfate, etc.; the lubricant and cosolvent may be talc, silica, stearate, tartaric acid, liquid paraffin, polyethylene glycol, etc.
The tablets may be further formulated into coated tablets, such as sugar-coated tablets, film-coated tablets, enteric-coated tablets, or double-layer and multi-layer tablets.
To encapsulate the administration unit, the active ingredient of the compound of the present invention may be mixed with a diluent and a cosolvent, and the mixture may be directly placed in a hard capsule or soft capsule. Or the effective component of the compound of the invention can be prepared into granules or pellets with diluent, adhesive and disintegrating agent, and then placed into hard capsules or soft capsules. The diluents, binders, wetting agents, disintegrants, and cosolvents used to prepare the compound tablets of the present invention can also be used to prepare capsules of the compounds of the present invention.
For preparing the compound of the present invention into injection, water, ethanol, isopropanol, propylene glycol or their mixture can be used as solvent, and appropriate amount of solubilizer, cosolvent, pH regulator, and osmotic pressure regulator commonly used in the art can be added. The solubilizer or cosolvent can be poloxamer, lecithin, hydroxypropyl-beta-cyclodextrin, etc.; the pH regulator can be phosphate, acetate, hydrochloric acid, sodium hydroxide, etc.; the osmotic pressure regulator can be sodium chloride, mannitol, glucose, phosphate, acetate, etc. For example, mannitol and glucose can be added as proppant for preparing lyophilized powder for injection.
In addition, colorants, preservatives, flavors, or other additives may also be added to the pharmaceutical preparation, if desired.
For the purpose of administration and enhancing the therapeutic effect, the drug or pharmaceutical composition of the present invention can be administered by any known administration method.
The dosage of the pharmaceutical composition of the compound of the present invention to be administered may vary widely depending on the nature and severity of the disease to be prevented or treated, the individual condition of the patient or animal, the route and dosage form of administration, and the like. Generally, a suitable daily dosage range for a compound of the invention is 0.001-5mg/Kg body weight. The above-described dosage may be administered in one dosage unit or divided into several dosage units, depending on the clinical experience of the physician and the dosage regimen including the use of other therapeutic means.
The compounds or compositions of the present invention may be administered alone or in combination with other therapeutic or symptomatic agents. When the compound of the present invention is used in a synergistic manner with other therapeutic agents, the dosage thereof should be adjusted according to the actual circumstances.
The fourth aspect of the technical scheme of the invention provides the application of the mixed source terpenoid (-) -hyperterpenoid B and pharmaceutically acceptable salts thereof in preparing anti-inflammatory drugs.
Advantageous technical effects
The invention tests the anti-inflammatory activity of (-) -hyperterpnoid B in a model for generating inflammatory factor NO of primary mouse abdominal cavity macrophages induced by LPS, and experiments prove that the (-) -hyperterpnoid B can obviously inhibit the generation of the inflammatory factor NO of the primary mouse abdominal cavity macrophages induced by LPS and shows obvious anti-inflammatory activity. Therefore, (-) -hyperterpenoid B of the invention can be used for preparing anti-inflammatory drugs.
Detailed Description
The chemical structural formula of (-) -Hyperterpineol B (the Arabic numerals in the structural formula are the index positions of carbon atoms in the chemical structure) referred to in the examples is as follows:
preparation of (-) -Hyperterpineol B as described in example 1
Extraction: pulverizing aerial part 30.0kg of dried herba Lysimachiae Foenumgraeci (Hypericum benii), extracting with 95% ethanol (150L) under reflux at 80 deg.C for 3 times, and concentrating the extractive solution under reduced pressure at 37 deg.C to obtain crude extract (1990.3 g); dissolving the crude extract (1990.3g) in water (2000mL), suspending uniformly, extracting with petroleum ether (2000mL) for three times, and concentrating the obtained extract under reduced pressure (37 deg.C) to obtain petroleum ether extract (998.5 g).
Separation: petroleum ether extract (998.5g) was subjected to silica gel (200-300 mesh) column chromatography, eluting with a petroleum ether/ethyl acetate gradient.
The concentration of petroleum ether/ethyl acetate gradient elution is 1: 0,20: 1,9: 1,4: 1,1: 1,0: 1, the volume of eluent per concentration was 2500ml, and two column volumes (2X 2500ml) were eluted per concentration.
Combining similar fractions according to TLC color development (anisaldehyde color development agent) to obtain 12 components Fr.1-12;
wherein the component Fr.3(55g), i.e. the petroleum ether/ethyl acetate volume ratio 20: 1, further performing silica gel (300-400 mesh) column chromatography on the eluted fraction, and purifying with petroleum ether/acetone 4: 1 volume ratio elution, volume of eluent 950ml, elution of two column volumes (2X 950 ml).
Similar fractions were combined according to TLC coloration (anisaldehyde coloration) to give 6 fractions A-F.
Component E (6.2g) was further subjected to column chromatography on silica gel (300-400 mesh) eluting with a petroleum ether/ethyl acetate gradient.
The concentration of petroleum ether/ethyl acetate gradient elution is 1: 0,9: 1,4: 1,2: 1,0: 1, the volume of eluent of each concentration was 450ml, and two column volumes (2X 450ml) were eluted per concentration.
Similar fractions were combined according to TLC coloration (anisaldehyde coloration) to give 7 fractions with a petroleum ether/ethyl acetate volume ratio of 2: 1 fraction, fraction E5(332mg).
Purification by preparative HPLC [ C18 column (10 μm, 250 × 20mm) methanol/water 85: elution at a volume ratio of 15, a flow rate of 6mL/min and a detection retention time of 25.2min at a wavelength of 254nm gave (-) -Hyperterpnoid B (7.0mg) of the present invention.
And (3) structural identification: the chemical structure of the compound (-) -Hyperterpnoid B is determined by a plurality of modern spectral techniques such as NMR, HRESIMS, UV, IR, optical rotation and the like, and the physicochemical properties are as follows:
yellow needle-like with molecular formula of
Ultraviolet spectrum UV (MeOH) lambdamax(log)235(4.13)，322(3.32)nm；
Infrared Spectrum IR (KBr) vmax：2977cm-1、1707cm-1；
High resolution mass spectrum HRESIMS M/z 509.19540[ M + H ]]+(calculated for C32H29O6,509.19696)；
Hydrogen spectrum of nuclear magnetic resonance1H NMR (500MHz) and NMR carbon Spectroscopy13C NMR (125MHz) data are shown in Table I,
TABLE 1 preparation of the (-) -Hyperterpnoid B1H13C and NMR (ppm in CDCl)3)
Example 2(-) -Hyperterpinenid B inhibition of LPS-induced production of inflammatory factor NO by peritoneal macrophages in primary mice.
Experimental sample
Preparation of a tested sample solution: the test sample was the pure compound prepared in example 1 ((-) -hypertene B). An appropriate amount of sample is accurately weighed, and DMSO is used for preparing a solution of 10umol/L for testing the pharmacological activity.
Cell lines: primary mouse peritoneal macrophages. Macrophages perform the nonspecific immune function of an organism, can generate inflammatory factors such as NO and the like under the induction of bacterial Lipopolysaccharide (LPS), participate and mediate inflammatory reaction, and have higher levels in the initial stage of various inflammatory immune processes and the pathological development process. By detecting the NO production amount of the primary cultured mouse macrophage, the method can be used as an index for preliminarily observing and screening components or compounds with certain anti-inflammatory activity in vitro.
Experimental methods
Inoculating primary mouse abdominal cavity macrophage to 96-well plate, adding compound (10) to be tested-5M) and a positive control drug dexamethasone (Dex) for 1 h; then, 1. mu.g/ml LPS was added at 37 ℃ with 5% CO2After 24 hours of culture in an incubator, the supernatant was collected, and the NO content (NO inhibition%) was measured by the Griess method, and the cell proliferation inhibition was measured by the MTT method.
Results of the experiment
Under the current experimental scheme, LPS (lipopolysaccharide) at the concentration of 10 mu M induces the generation of the inflammatory factor NO of the abdominal cavity macrophage of the primary mouse to show obvious inhibition activity (the NO generation inhibition rate is 80.12 percent), and a positive control group (Dexamethasone, Dexamethasone: the NO generation inhibition rate is 55.10 percent) is shown in the table 1.
TABLE 1 Effect on LPS-induced generation of macrophage NO from Primary mouse peritoneal
Conclusion of the experiment
The compound (-) -hyperterpnoid B has obvious inhibitory activity on the generation of primary mouse abdominal cavity macrophage inflammatory factor NO induced by LPS and shows obvious anti-inflammatory effect, so the (-) -hyperterpnoid B can be used for preparing anti-inflammatory drugs.
Claims (9)
1. A mixed source terpenoid shown as a formula (I) and pharmaceutically acceptable salts thereof:
2. the method for preparing the mixed source terpenoid of claim 1, comprising the following steps:
extraction: extracting the ground aerial parts of the yellow flower fragrance Hypericum benii with ethanol, and concentrating the obtained extract to obtain a crude extract; dissolving the crude extract in water, suspending uniformly, extracting with petroleum ether, and concentrating the obtained extract to obtain petroleum ether extract;
separation: performing silica gel column chromatography on the petroleum ether extract, and performing gradient elution by using petroleum ether/ethyl acetate, wherein the volume ratio of the petroleum ether/ethyl acetate is 20: 1, and further performing silica gel column chromatography on the eluted part of the crude product in a petroleum ether/acetone volume ratio of 4: 1, and further performing silica gel column chromatography on the eluent, and performing gradient elution by using petroleum ether/ethyl acetate, wherein the volume ratio of the petroleum ether to the ethyl acetate is 2: 1 by preparative high performance liquid HPLC, in a methanol/water volume ratio of 85: 15 to obtain the target compound (-) -hyperterpenoid B.
3. The method of claim 2, wherein the ethanol used in the extracting step is 95% ethanol.
4. The method according to claim 2, wherein the extraction step is carried out by heating and refluxing.
5. The method according to claim 2, wherein in the separation step, the concentration of the first petroleum ether/ethyl acetate gradient elution is in the order of volume ratio of 1: 0,20: 1,9: 1,4: 1,1: 1,0: 1.
6. the method according to claim 2, wherein in the separation step, the concentration of the second petroleum ether/ethyl acetate gradient elution is in the order of volume ratio of 1: 0,9: 1,4: 1,2: 1,0: 1.
7. the method according to claim 2, wherein the column packing of preparative high performance liquid HPLC is reverse-phase octadecyl bonded silica gel in the separation step.
8. A pharmaceutical composition comprising the mixed-source terpenoid of claim 1 and a pharmaceutically acceptable salt or an additive thereof.
9. Use of the mixed-source terpenoid of claim 1 and pharmaceutically acceptable salts thereof for the preparation of anti-inflammatory drugs.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6245362B1 (en) * | 1995-12-18 | 2001-06-12 | Dreluso Pharmazeutika Dr. Elten & Sohn Gmbh | Medication for treatment of viral disease based on active agents of plant hypericum (St. John's Wort) and method of production of the medication |
| US20030065023A1 (en) * | 2001-03-23 | 2003-04-03 | Swindell Charles S. | Fatty amine drug conjugates |
| JP2004359565A (en) * | 2003-06-03 | 2004-12-24 | Hosoda Shc:Kk | Prostaglandin e2 release inhibitor |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6245362B1 (en) * | 1995-12-18 | 2001-06-12 | Dreluso Pharmazeutika Dr. Elten & Sohn Gmbh | Medication for treatment of viral disease based on active agents of plant hypericum (St. John's Wort) and method of production of the medication |
| US20030065023A1 (en) * | 2001-03-23 | 2003-04-03 | Swindell Charles S. | Fatty amine drug conjugates |
| JP2004359565A (en) * | 2003-06-03 | 2004-12-24 | Hosoda Shc:Kk | Prostaglandin e2 release inhibitor |
Non-Patent Citations (6)
| Title |
|---|
| BO ZHEN等: "Hyperterpenoids A and B:Two pairs of unprecedented 6/6/4/6/6 polycyclic cyclobutane meroterpenoids with potent neuroprotective and anti-inflammatory activities from Hypericum beanii", 《CHINESE CHEMICAL LETTERS》 * |
| SARA L.CROCKETT等: "Anti-inflammatory phloroglucinol derivatives from Hypericum empetrifolium", 《PHYTOCHEMISTRY LETTERS》 * |
| ZAI-YING WANG等: "Lecanicillones A–C,three dimeric isomers of spiciferone A with a cyclobutane ring from an entomopathogenic fungus Lecanicillium sp. PR-M-3", 《RSC ADVANCES》 * |
| 徐晓诗等: "金丝桃化学成分的研究", 《中草药》 * |
| 杨明惠等: "黄花香茶菜的二萜成分研究", 《中草药》 * |
| 肖志勇等: "金丝桃属植物化学成分研究进展", 《天然产物研究与开发》 * |
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