CN113402528A - Cedarane type macrocyclic diterpenoid compound, preparation method, pharmaceutical composition and application - Google Patents
Cedarane type macrocyclic diterpenoid compound, preparation method, pharmaceutical composition and application Download PDFInfo
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Abstract
The invention relates to the technical field of medicines, and particularly discloses a series of cembrane type macrocyclic diterpenoid compounds extracted and separated from frankincense (Boswellia sacra fluent) resin, and a preparation method, a pharmaceutical composition and application thereof. Pharmacological research shows that the obtained compounds have obvious nerve cell protection effect in a primary neuron cell model damaged by glutamic acid and an oxygen sugar deprivation damage model, and the compounds have good medicinal prospect in preparing nerve cell protection medicaments.
Description
Technical Field
The invention relates to the technical field of medicines. Relates to a series of cembrane type macrocyclic diterpenoid compounds extracted and separated from frankincense (Boswellia sacra Flueck) resin, a preparation method thereof and application thereof in the preparation of nerve cell protective drugs.
Background
The cembrane diterpene is one of the most abundant diterpenes, and has a 14-membered ring parent nucleus skeleton formed by head-to-head connection of 4 isoprene units. Such compounds are found in marine organisms, particularly in the genus Sarcophyton and Cereus. A few cembrane diterpenoid compounds are found in terrestrial plants such as tobacco, pine and myrrh, in recent years, a plurality of cembrane diterpenoid compounds are separated from frankincense in sequence, and pharmacological activity researches show that the cembrane diterpenoid compounds have good activities of resisting inflammation, resisting depression, resisting enteritis, resisting bacteria, resisting tumors and the like.
The mastic is a gum resin exuded from the bark or by cutting of Boswellia carterii (Boswellia carterii Birdw) belonging to Boswellia (Boswellia carterii Birdw) of Boswellia of the family Burseraceae and Boswellia bhawdajiana (Boswellia bhawdajiana Birdw) belonging to the same genus, mainly produced in Somalia, Elisa, India, etc., and is a commonly used Chinese medicine. The frankincense with pungent flavor can disperse warm and dredge, and has the effects of regulating qi, activating blood, relieving pain and dispelling toxin. Can be used for treating stagnation of qi and blood, pain of heart and abdomen, carbuncle, sore, toxic swelling, traumatic injury, dysmenorrhea, and puerperal blood stasis and pain; the main components of the frankincense are tetracyclic triterpene, pentacyclic triterpene and macrocyclic diterpenoid compounds, and modern pharmacological research shows that the compounds also have good activities of resisting inflammation, resisting tumors and the like. Wherein the nerve cell protection activity of the cembrane macrocyclic diterpenoid compound is not reported.
Disclosure of Invention
The invention aims to provide a cembrane diterpenoid compound separated and purified from frankincense, a preparation method and a pharmaceutical composition thereof, and application of the compound in preparing nerve cell protection medicaments.
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 cembrane macrocyclic diterpenoid compound and pharmaceutically acceptable salts thereof, which are respectively named as compound 1(bossacrin E), compound 2(bossacrin J) and compound 3(bossacrin G), and the structural formulas of the compounds are respectively as follows:
the second aspect of the technical scheme of the invention provides a method for separating and purifying cembrane diterpene from frankincense.
Technical solution a process for preparing compound 1 according to the first aspect comprises the steps of:
(1) pulverizing Olibanum material, and extracting with 95% ethanol under reflux for 3 hr each time for three times. Mixing the extractive solutions, and removing solvent to obtain Olibanum crude extract.
(2) Subjecting the crude extract of Olibanum to silica gel column chromatography, sequentially eluting with two parts of petroleum ether, two parts of ethyl acetate, and two parts of 95% ethanol, each part having a column volume. Crude sections A-F are obtained.
(3) And (3) performing silica gel column chromatography on the crude segment A, and performing gradient elution by using petroleum ether ethyl acetate according to the volume ratio of 1:0, 20:1, 4:1, 1:1 and 0:1, wherein two column volumes are eluted in each gradient.
(4) And (3) carrying out silica gel column chromatography on the first crude part A5 eluted by petroleum ether and ethyl acetate in a volume ratio of 4:1 in the step (3), eluting by using dichloromethane and acetone in a volume ratio of 30:1, and combining similar components to obtain fractions A-5-1-A-5-12.
(5) Taking the fraction A-5-2, preparing by a reversed phase C18 semi-preparative high performance liquid method, taking methanol and water in a volume ratio of 85:15 as a mobile phase, and detecting the wavelength of 210nm to obtain the compound 1.
The compound 1 has a structural formula:
technical solution in a first aspect, the preparation method of compounds 2 and 3 comprises the following steps:
(1) pulverizing Olibanum material, and extracting with 95% ethanol under reflux for 3 hr each time for three times. Mixing the extractive solutions, and removing solvent to obtain Olibanum crude extract.
(2) Subjecting the crude extract of Olibanum to silica gel column chromatography, sequentially eluting with two parts of petroleum ether, two parts of ethyl acetate, and two parts of 95% ethanol, each part having a column volume. Crude sections A-F are obtained.
(3) And (3) performing silica gel column chromatography on the crude segment A, and performing gradient elution by using petroleum ether ethyl acetate according to the volume ratio of 1:0, 20:1, 4:1, 1:1 and 0:1, wherein two column volumes are eluted in each gradient.
(4) And (3) carrying out silica gel column chromatography on the first crude part A5 eluted by petroleum ether and ethyl acetate in a volume ratio of 4:1 in the step (3), eluting by using dichloromethane and acetone in a volume ratio of 30:1, and combining similar components to obtain fractions A-5-1-A-5-12.
(5) Taking the flow part A-5-5, preparing by adopting a reverse phase C18 semi-preparative high performance liquid method, taking methanol and water with the volume ratio of 82:18 as a mobile phase, and detecting the wavelength of 210nm to obtain the compounds 2 and 3.
The structural formulas of the compounds 2 and 3 are as follows:
in a third aspect of the technical scheme of the present invention, a pharmaceutical composition is provided, wherein the pharmaceutical composition comprises the cembrane diterpene compound of the first aspect and a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable carrier or excipient.
The fourth aspect of the technical scheme of the invention provides application of the cembrane diterpenoid compound and the pharmaceutically acceptable salt thereof in preparing nerve cell protection medicaments
In the present invention, the above-mentioned compound was measured and evaluated for its protective effect on glutamate-induced cortical neuron damage in vitro, and the results showed that compound 2 showed a protective effect on glutamate-induced cortical neuron damage at a concentration of 10. mu.M, comparable to that of the positive control.
In the present invention, the measurement and evaluation of the protective effect of oxygen-sugar deprived cortical neuron hypoxia injury were also carried out in vitro on the above-mentioned compounds, and the results showed that Compound 1 showed superior protective effect on oxygen-sugar deprived cortical neuron hypoxia injury to that of the positive control at a concentration of 10. mu.M.
Advantageous technical effects
1. The invention separates and purifies three cembrane diterpenoid compounds 1,2 and 3 from frankincense for the first time.
2. The method for determining and evaluating the protection effect of the monomeric compound on the glutamic acid-induced cortical neuron cell damage proves that the compounds all show a certain protection effect on the glutamic acid-induced cortical neuron damage under the concentration of 10 mu M, wherein the compound 2 has the optimal effect and good medicinal prospect.
3. The method for determining and evaluating the protection effect of the monomeric compound on the oxygen-sugar-deprived cortical neuron hypoxia injury proves that the compound 1 shows better protection effect on the oxygen-sugar-deprived cortical neuron hypoxia injury under the concentration of 10 mu M, and has good medicinal prospect.
Drawings
The drawings in the present application are intended to provide further explanation of the application, and the illustrative embodiments and description of the application are intended to explain the application and are not to be construed as limiting the application.
FIG. 1 preparation of Compound 1(bossacrin E)1H NMR
FIG. 2 preparation of Compound 1(bossacrin E)13C NMR
FIG. 3 HRESIMS of Compound 1(bossacrin E)
FIG. 4. of Compound 2(bossacrin J)1H NMR
FIG. 5 preparation of Compound 2(bossacrin J)13C NMR
FIG. 6 HRESIMS of Compound 2(bossacrin J)
FIG. 7 preparation of Compound 3(bossacrin G)1H NMR
FIG. 8 preparation of Compound 3(bossacrin G)13C NMR
FIG. 9 HRESIMS of Compound 3(bossacrin G)
Detailed Description
To further illustrate the present invention, the following detailed description of the invention is given by way of specific examples, which are purely illustrative and intended to describe the invention in detail and not intended to limit the exemplary embodiments according to the application.
Pharmaceutical chemistry experiments:
example 1
Preparation of Compounds 1-3, the procedure was as follows:
(1) crushing 19.0kg of frankincense medicinal material, and performing heating reflux extraction with 95% ethanol at a solid-liquid ratio of 1:3.5(kg/L) for 3h each time, wherein the extraction is performed for three times. Mixing the extractive solutions, and rotary evaporating the solvent under reduced pressure to obtain Olibanum crude extract.
(2) Subjecting the crude extract of Olibanum to silica gel column chromatography, sequentially eluting with two parts of petroleum ether, two parts of ethyl acetate, and two parts of 95% ethanol, each part receiving a column volume of about 35L. Crude sections A-F are obtained.
(3) And (3) performing silica gel column chromatography on the crude segment A, and performing gradient elution by using petroleum ether ethyl acetate according to the volume ratio of 1:0, 20:1, 4:1, 1:1 and 0:1, wherein each gradient elutes two column volumes, and each column volume receives one column volume, namely about 5L.
(4) And (3) carrying out silica gel column chromatography on the first crude part A5 eluted by petroleum ether and ethyl acetate in a volume ratio of 4:1 in the step (3), eluting by using dichloromethane and acetone in a volume ratio of 30:1, and combining similar components to obtain fractions A-5-1-A-5-12.
(5) Taking the fraction A-5-2, and preparing by reverse phase C18 semi-preparative high performance liquid chromatography with MeOH/H2O (85: 15) was prepared as a mobile phase at a flow rate of 3ml/min and a detection wavelength of 210nm to give Compound 1.
(6) Taking the fraction A-5-5, preparing by reverse phase C18 semi-preparative high performance liquid method with MeOH/H2O (82: 18) was prepared as a mobile phase at a flow rate of 3ml/min and a detection wavelength of 210nm to give compounds 2 and 3.
And (3) structural identification: the structures of 3 new compounds are determined by the methods of nuclear magnetic resonance hydrogen spectrum, nuclear magnetic resonance carbon spectrum, mass spectrum, two-dimensional nuclear magnetic resonance spectrum and the like for the separated compounds. See fig. 1-9.
Compound 1: bossacrin E, colorless oil, anisaldehyde-sulfuric acid purple. Optical rotation value [ alpha ]]20D +18.7(c 0.18, MeOH); maximum UV absorption value UV (MeOH) lambdamax(log ε)204.0 (2.92); infrared spectral data IR vmax 3415,2960,1736,1468,1436,1370,1239,1038cm-1；1H NMR and13the C NMR data are shown in Table 1. HRESIMS M/z 387.25009[ M + Na ]]+Calculated value is C20H36O4Na：m/z 387.25058。
Compound 2: bossacrin J, colorless oil, anisaldehyde-sulfuric acid purple. Optical rotation value [ alpha ]]20D-87.8(c 0.13, MeOH); maximum UV absorption value UV (MeOH) lambdamax(log ε)204.0 (3.10); infrared spectral data IR vmax 3297,2924,1643,1440,1376,1039,1005,888cm-1；1H NMR and13the CNMR data are shown in Table 1. HRESIMS M/z 327.22916[ M + Na ]]+Calculated value is C20H32O2Na,327.22945。
Compound 3: bossacrin G, colorless oil, anisaldehyde-sulfuric acid purple. Optical rotation value [ alpha ]]20D-16.2(c 0.08, MeOH); maximum UV absorption value UV (MeOH) lambdamax(log ε)204.0 (2.55); infrared spectral data IR vmax 3452,2960,2927,1731,1715,1461,1371,1244,1045cm-1；1H NMR and13the C NMR data are shown in Table 1. HRESIMS M/z 387.25043[ M + Na ]]+Calculated value is C20H36O4Na：m/z 387.25058.
TABLE 1 preparation of Compounds 1-31H NMR and13c NMR data
Pharmacological experiment:
experimental example 1
The neuroprotective effect of the screening compounds 1-3 was evaluated using a fetal rat primary neuronal glutamate model, an SK-N-SH cell triphosgene oxygen deprivation model.
1. Materials and reagents: cortical neurons of wistar rat embryos at day 17 of pregnancy (glutamate model), damaging agent glutamate (final concentration: 200 μ M); the 14 th generation of SK-N-SH cells (oxygen sugar deprivation model in a three-gas incubator), a low-sugar culture medium and an anoxic device; compound was screened and positive PHPB (final concentration 10. mu.M).
2. Method of producing a composite material
1) Glutamate injury model: cortical neurons from Wistar rat embryos taken from day 17 of pregnancy were cultured. One week later, the pre-incubated positive tool drug PHPB (10. mu. mol/L)/screen compound (10. mu. mol/L) was used for 1 hour. Glutamic acid diluent with a final concentration of 200. mu.M and PHPB/compound with a final concentration of 10uM were added to each well, and after 20 hours of co-culture, the cell viability was examined by the MTT method.
2) Oxygen sugar deprivation model of three-gas hypoxia device: SK-N-SH cells are plated and cultured. One week later, positive tool PHPB (10 umol/L)/sieving compound (10umol/L) were incubated with SK-N-SH cells for 1 hour, respectively. And (3) carrying out anoxic and sugar-deficient culture for 5.5h in a three-gas culture box, carrying out reoxygenation for 20h, and detecting the cell survival rate by an MTT method.
3) The experimental grouping is normal control group, model group: glutamic acid group (final concentration: 200uM)/OGD group, positive tool PHPB group (final concentration: 10umol/L), each screening compound group.
3. Results of the experiment
1) Glutamic acid model:
TABLE 2 Effect of Compounds 1-3 on survival of fetal rat Primary neuronal cell glutamate model cells
P <0.001 compared to control; # P <0.05 vs. model group, # P <0.01 vs. model group, # P <0.001 vs. model group
2) Oxygen sugar deprivation model:
TABLE 3 Effect of Compounds 1-3 on the survival of SK-N-SH cells in an oxygen deprivation model.
P <0.001 compared to control; # P <0.05 vs. model group, # P <0.01 vs. model group, # P <0.001 vs. model group
4. Discussion and conclusions of the experiments:
the experiment uses a primary neuron glutamic acid model and an SK-N-SH cell trioxyglucose deprivation model to evaluate whether the compound has the neuroprotective effect, and the experimental result shows that:
(1) glutamic acid model:
1) the glutamic acid damages the primary neurons for 20h, so that the cell survival rate of the primary neurons of the model group is respectively reduced to 53.1%, and the successful establishment of the glutamic acid model is shown.
2) The positive tool drug PHPB (10mmol/L) had a tendency to neuroprotective.
3) The compound 2 can improve the survival rate of primary neuron cells damaged by glutamic acid in a glutamic acid damage model, and has the function of protecting nerve cells in the model.
(1) Oxygen sugar deprivation model of three-gas device:
1) after the oxygen-sugar deprivation model of the three-gas device is reoxygenated for 20h, the survival rates of SK-N-SH cells can be obviously reduced to 65.3%, which indicates that the oxygen-sugar deprivation model is successfully established.
2) The positive tool medicine PHPB (10mmol/L) has neuroprotective effect.
3) In the model screening, the compound 1 can obviously improve the survival rate of oxygen-deprived SK-N-SH cells, and has the function of protecting nerve cells in the model.
The above description is only a preferred example of the present application and is not intended to limit the present application. Any modification, equivalent replacement, improvement and the like made to the present application within the central idea and principle of the present application should be included in the protection scope of the present application.
Claims (6)
1. A cembrane macrocyclic diterpenoid compound and its pharmaceutically acceptable salt, characterized by, it is compound 1-3, the structural formula is:
2. a process for the preparation of a cembrane-type macrocyclic diterpene compound as claimed in claim 1, which comprises the steps of:
(1) crushing a frankincense medicinal material, and then performing heating reflux extraction by using 95% ethanol, wherein the extraction is performed for 3 hours each time and is performed for three times; mixing the extractive solutions, and removing solvent to obtain Olibanum crude extract;
(2) subjecting the crude extract of Olibanum to silica gel column chromatography, sequentially eluting with two parts of petroleum ether, two parts of ethyl acetate and two parts of 95% ethanol, each part having a column volume to obtain crude segments A-F;
(3) performing silica gel column chromatography on the crude section A, and performing gradient elution by using petroleum ether ethyl acetate, wherein the volume ratio of the petroleum ether ethyl acetate is 1:0, 20:1, 4:1, 1:1 and 0:1 in sequence, and each gradient elution has two column volumes;
(4) performing silica gel column chromatography on the first crude part A5 eluted by the petroleum ether and ethyl acetate in the step (3) at the volume ratio of 4:1, eluting by dichloromethane and acetone at the volume ratio of 30:1, and combining similar components to obtain fractions A-5-1-A-5-12;
(5) taking the fraction A-5-2, preparing by adopting a reverse phase C18 semi-preparative high performance liquid method, taking methanol and water in a volume ratio of 85:15 as a mobile phase, and detecting the wavelength of 210nm to obtain a compound 1;
(6) taking the flow part A-5-5, preparing by adopting a reverse phase C18 semi-preparative high performance liquid method, taking methanol and water with the volume ratio of 82:18 as a mobile phase, and detecting the wavelength of 210nm to obtain the compounds 2 and 3.
3. The method as claimed in claim 2, wherein the ratio of the mass of the boswellia carterii of step (1) to the volume of the 95% ethanol used each time is 1Kg to 3.5L.
4. The method as set forth in claim 2, wherein the solvent is removed in the step (1) by rotary evaporation under reduced pressure.
5. A pharmaceutical composition comprising the cembrane-type macrocyclic diterpene compound of claim 1 and a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable carrier or excipient.
6. Use of the cembrane-type macrocyclic diterpene compound as claimed in claim 1 and its pharmaceutically acceptable salts for the preparation of neuroprotective drugs.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114019019A (en) * | 2021-11-10 | 2022-02-08 | 天津师范大学 | Quartz crystal microbalance sensor and detection of mustard gas and mustard gas simulants by quartz crystal microbalance sensor |
Citations (5)
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| JPS5661318A (en) * | 1979-10-26 | 1981-05-26 | Mitsubishi Chem Ind Ltd | Cembranolide diterpen |
| EP0455826A1 (en) * | 1989-11-29 | 1991-11-13 | Mitsubishi Chemical Corporation | Substituted open-chain terpene compound |
| US20050250752A1 (en) * | 2002-05-09 | 2005-11-10 | Ziawiony Jordan K | Cembranoids with chemopreventive activity |
| CN102481265A (en) * | 2009-07-14 | 2012-05-30 | 莫尔豪斯医学院 | Methods and compositions for protecting and treating neuroinjury |
| CN108640890A (en) * | 2018-04-10 | 2018-10-12 | 山东省分析测试中心 | A method of isolating and purifying frankincense Chinese and Western pine alkane type macrocyclic diterpene compounds |
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2020
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5661318A (en) * | 1979-10-26 | 1981-05-26 | Mitsubishi Chem Ind Ltd | Cembranolide diterpen |
| EP0455826A1 (en) * | 1989-11-29 | 1991-11-13 | Mitsubishi Chemical Corporation | Substituted open-chain terpene compound |
| US20050250752A1 (en) * | 2002-05-09 | 2005-11-10 | Ziawiony Jordan K | Cembranoids with chemopreventive activity |
| CN102481265A (en) * | 2009-07-14 | 2012-05-30 | 莫尔豪斯医学院 | Methods and compositions for protecting and treating neuroinjury |
| CN108640890A (en) * | 2018-04-10 | 2018-10-12 | 山东省分析测试中心 | A method of isolating and purifying frankincense Chinese and Western pine alkane type macrocyclic diterpene compounds |
Non-Patent Citations (1)
| Title |
|---|
| TZU-YIN HUANG等: "New Hydroquinone Monoterpenoid and Cembranoid-Related Metabolites from the Soft Coral Sarcophyton tenuispiculatum", 《MARINE DRUGS》, vol. 19, no. 1, pages 1 - 11 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114019019A (en) * | 2021-11-10 | 2022-02-08 | 天津师范大学 | Quartz crystal microbalance sensor and detection of mustard gas and mustard gas simulants by quartz crystal microbalance sensor |
| CN114019019B (en) * | 2021-11-10 | 2024-05-24 | 天津师范大学 | Quartz crystal microbalance sensor and detection of mustard gas and mustard gas simulants thereof |
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