CN113861008A - Botrytis macrocarpa rosin diterpene, preparation method thereof and application of botrytis macrocarpa rosin diterpene in preparation of anti-inflammatory and antibacterial medicines for preventing or/and treating inflammation - Google Patents
Botrytis macrocarpa rosin diterpene, preparation method thereof and application of botrytis macrocarpa rosin diterpene in preparation of anti-inflammatory and antibacterial medicines for preventing or/and treating inflammation Download PDFInfo
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- CN113861008A CN113861008A CN202111051450.XA CN202111051450A CN113861008A CN 113861008 A CN113861008 A CN 113861008A CN 202111051450 A CN202111051450 A CN 202111051450A CN 113861008 A CN113861008 A CN 113861008A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/46—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing hydroxy groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract
The invention relates to the technical field of separation and purification of bract catnip, in particular to a bract rosin diterpenoid, a preparation method thereof and application thereof in preparing anti-inflammatory and antibacterial medicaments for preventing or/and treating inflammation. The invention discloses a compound 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nebetabutyrate B) for the first time, and in-vitro anti-inflammatory and antibacterial pharmacodynamic experiments are carried out on the compound, and the experiments show that the compound has stronger inhibition effect on RAW 264.7 cells, staphylococcus aureus and escherichia coli, so that the compound can be used for preparing anti-inflammatory and antibacterial drugs or/and preparing health-care products for preventing and treating inflammation and inhibiting bacteria.
Description
Technical Field
The invention relates to the technical field of separation and purification of schizonepeta bracteata, in particular to a bracteatum rosin diterpene, a preparation method thereof and application thereof in preparing anti-inflammatory and antibacterial medicines for preventing or/and treating inflammation, wherein the bracteatum rosin diterpene is the abbreviation of 1,2,3,4,4a,9,10,10a-octahydro-2-hydroxy-7-isopropyl-1,4 a-methylenephenanthrene-1-carbaldehyde (nepetabutyrate B).
Background
Nepeta bracteata Benth is a Nepeta plant of Labiatae Nepeta genus Nepeta, mainly distributed in Pakistan, Nepal, Iran and other countries, named as 'ancestral', and known as Shenvanica, and has wide clinical application mainly in import. The whole herbs are used as the medicine, have slight faint scent, light taste and slight dampness, enter lung and liver channels, have the functions of relieving cough and asthma, clearing heat and promoting diuresis, and are clinically used for treating symptoms such as tracheitis, cough and asthma, cold and fever, dysuria and the like. In addition, the schizonepeta cataria has the characteristics of easy source, low cost, reliable clinical curative effect, small toxic and side effects and the like. So far, the emphasis on the research of the schizonepeta bracteata and basic theoretical research are not abundant, and modern pharmacology shows that the extract of the schizonepeta bracteata has obvious anti-inflammatory and antibacterial activities, but related research on chemical components is not carried out, and the schizonepeta bracteata is probably a good species for treating respiratory diseases, so that the schizonepeta bracteata is concerned by people in recent years.
The medicinal effect of the schizonepeta cataria is mainly derived from terpenoids in the schizonepeta cataria, including monoterpenes and diterpenoids, wherein diterpenoids as the main components have better anti-inflammatory and bacteriostatic activities, so that the diterpenoid monomeric compounds of the schizonepeta cataria are developed and utilized, the potential medicinal value of the monomeric compounds of the schizonepeta cataria is further excavated, and the structure and the physicochemical properties of the monomeric compounds of the schizonepeta cataria are determined and characterized, thereby having important significance for developing and utilizing the schizonepeta cataria.
Disclosure of Invention
The invention provides 1,2,3,4,4a,9,10,10 a-octahydrophe-2-hydroxy-7-isoproyl-1, 4 a-dimethoxyantrene-1-carbaldehyde (nepetabutyrate B) and a preparation method and application thereof, overcomes the defects of the prior art, and discloses 1,2,3,4,4a,9,10,10 a-octahydrophe-2-hydroxy-7-isoproyl-1, 4 a-dimethoxyanthrene-1-carbaldehyde (nepetabutyrate B) for the first time and application thereof in preparing inflammation prevention and bacteriostasis medicaments or/and preparing anti-inflammatory and antibacterial medicaments or/and preparing health-care products for preventing and inhibiting inflammation and bacteriostasis.
One of the technical schemes of the invention is realized by the following measures: 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) with a chemical structural formula
The following is a further optimization or/and improvement of one of the above-mentioned technical solutions of the invention:
the preparation method comprises the following steps: crushing the schizonepeta bracteata, adding ethanol, soaking for 3-4 hours at room temperature, heating and refluxing for 3 times at 50-60 ℃, extracting for 1-3 hours each time, combining the refluxing extracting solutions each time, and recovering and concentrating under reduced pressure to obtain a schizonepeta bracteatum total extract; secondly, dispersing the schizonepeta tenuifolia total extract by using water, and sequentially extracting by using petroleum ether and dichloromethane to obtain a petroleum ether part and a dichloromethane part; and step three, performing gradient elution and separation on the extract at the petroleum ether part by using a silica gel column chromatography to obtain 8 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1: 0; and fourthly, performing gradient elution separation on the 6 th fraction in the obtained 8 fractions by using a silica gel column chromatography to obtain 5 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 20:1, 10:1 and 3: 1. 1:1, 0: 1; and fifthly, performing gradient elution separation on the 3 rd fraction in the obtained 5 fractions by using a silica gel column chromatography to obtain 3 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10:1, 5:1 and 3: 1; and sixthly, purifying and separating the 3 rd fraction in the 3 obtained fractions by high performance liquid chromatography gradient elution, collecting the eluate, and obtaining 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabromide B) at the 27.0 th minute.
In the first step, 8ml to 10ml of ethanol is added to every 1g of catalpa macrophylla.
In the sixth step, the eluent for gradient elution by high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
the second technical scheme of the invention is realized by the following measures: a preparation method of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) comprises the following steps: crushing the schizonepeta bracteata, adding ethanol, soaking for 3-4 hours at room temperature, heating and refluxing for 3 times at 50-60 ℃, extracting for 1-3 hours each time, combining the refluxing extracting solutions each time, and recovering and concentrating under reduced pressure to obtain a schizonepeta bracteatum total extract; secondly, dispersing the schizonepeta tenuifolia total extract by using water, and sequentially extracting by using petroleum ether and dichloromethane to obtain a petroleum ether part and a dichloromethane part; and step three, performing gradient elution and separation on the extract at the petroleum ether part by using a silica gel column chromatography to obtain 8 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1: 0; and fourthly, performing gradient elution separation on the 6 th fraction in the obtained 8 fractions by using a silica gel column chromatography to obtain 5 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 20:1, 10:1 and 3: 1. 1:1, 0: 1; and fifthly, performing gradient elution separation on the 3 rd fraction in the obtained 5 fractions by using a silica gel column chromatography to obtain 3 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10:1, 5:1 and 3: 1; and sixthly, purifying and separating the 3 rd fraction in the 3 obtained fractions by high performance liquid chromatography gradient elution, collecting the eluate, and obtaining 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabromide B) at the 27.0 th minute.
The following is further optimization or/and improvement of the second technical scheme of the invention:
in the first step, 8ml to 10ml of ethanol is added to every 1g of catalpa macrophylla.
In the sixth step, the eluent for gradient elution by high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
the third technical scheme of the invention is realized by the following measures: an application of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetalate B) in preparing the medicines for preventing inflammation and suppressing bacteria is disclosed.
The fourth technical scheme of the invention is realized by the following measures: an application of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) in preparing the medicines for anti-inflammation and antibacterial is disclosed.
The fifth technical scheme of the invention is realized by the following measures: an application of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methylenephenanthrene-1-carbaldehyde (nepetabutyrate B) in preparing the health-care products for preventing and treating inflammation and suppressing bacteria is disclosed.
The invention discloses a compound 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nebetabutyrate B) for the first time, and the compound is subjected to in vitro anti-inflammatory and antibacterial pharmacodynamics experiments, and the experiments show that the compound has stronger inhibition effect on RAW 264.7 cells, staphylococcus aureus and escherichia coli, so that the compound can be used for preparing anti-inflammatory and antibacterial drugs or/and health-care products for preventing and treating inflammation and inhibiting bacteria.
Drawings
FIG. 1 is a chemical structural diagram of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) according to the present invention.
FIG. 2 shows a schematic diagram of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) according to the present invention1H-NMR spectrum.
FIG. 3 shows a schematic diagram of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) according to the present invention13C-APT spectrum.
Detailed Description
The present invention is not limited by the following examples, and specific embodiments may be determined according to the technical solutions and practical situations of the present invention. The various chemical reagents and chemical articles mentioned in the invention are all the chemical reagents and chemical articles which are well known and commonly used in the prior art, unless otherwise specified; the percentages in the invention are mass percentages unless otherwise specified; the solution in the present invention is an aqueous solution in which the solvent is water, for example, a hydrochloric acid solution is an aqueous hydrochloric acid solution, unless otherwise specified; the normal temperature and room temperature in the present invention generally mean a temperature of 15 ℃ to 25 ℃, and are generally defined as 25 ℃.
The invention is further described below with reference to the following examples:
example 1: the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) is characterized in that the chemical structural formula is shown as
Subjecting 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) described in example 1 of the present invention to nuclear magnetic resonance hydrogen spectroscopy (NMR)1H-NMR) and nuclear magnetic resonance carbon Spectroscopy (C13C-APT).
The 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) described in this example1The H-NMR spectrum is shown in FIG. 2.
The 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) described in this example13The C-APT spectrum is shown in FIG. 3.
The chemical shift and peak type of carbon and hydrogen in the structure of compound 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthracene-1-carbaldehyde (nitrate B) are obtained by analyzing the map of FIG. 2 and FIG. 3 and assigning the peaks of FIG. 2 and FIG. 3, and the chemical structural formula is shown in FIG. 1. The peak assignments of fig. 2 and 3 are shown in table 1.
Example 2: the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methylenephenanthrene-1-carbaldehyde (nepetabutyrate B) is prepared by the following method: crushing the schizonepeta bracteata, adding ethanol, soaking for 3-4 hours at room temperature, heating and refluxing for 3 times at 50-60 ℃, extracting for 1-3 hours each time, combining the refluxing extracting solutions each time, and recovering and concentrating under reduced pressure to obtain a schizonepeta bracteatum total extract; secondly, dispersing the schizonepeta tenuifolia total extract by using water, and sequentially extracting by using petroleum ether and dichloromethane to obtain a petroleum ether part and a dichloromethane part; and step three, performing gradient elution and separation on the extract at the petroleum ether part by using a silica gel column chromatography to obtain 8 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1: 0; and fourthly, performing gradient elution separation on the 6 th fraction in the obtained 8 fractions by using a silica gel column chromatography to obtain 5 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 20:1, 10:1 and 3: 1. 1:1, 0: 1; and fifthly, performing gradient elution separation on the 3 rd fraction in the obtained 5 fractions by using a silica gel column chromatography to obtain 3 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10:1, 5:1 and 3: 1; and sixthly, purifying and separating the 3 rd fraction in the 3 obtained fractions by high performance liquid chromatography gradient elution, collecting the eluate, and obtaining 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabromide B) at the 27.0 th minute.
Example 3: as an optimization of the above embodiment, the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methylenephenanthrene-1-carbaldehyde (nepetabutyrate B) is prepared by the following method: crushing the schizonepeta bracteata, adding ethanol, soaking for 3 hours or 4 hours at room temperature, heating and refluxing for 3 times at 50 ℃ or 60 ℃ for 1 hour or 3 hours each time, combining the refluxing extracting solutions each time, and performing reduced pressure recovery and concentration to obtain a schizonepeta bracteatum total extract; secondly, dispersing the schizonepeta tenuifolia total extract by using water, and sequentially extracting by using petroleum ether and dichloromethane to obtain a petroleum ether part and a dichloromethane part; and step three, performing gradient elution and separation on the extract at the petroleum ether part by using a silica gel column chromatography to obtain 8 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1: 0; and fourthly, performing gradient elution separation on the 6 th fraction in the obtained 8 fractions by using a silica gel column chromatography to obtain 5 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 20:1, 10:1 and 3: 1. 1:1, 0: 1; and fifthly, performing gradient elution separation on the 3 rd fraction in the obtained 5 fractions by using a silica gel column chromatography to obtain 3 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10:1, 5:1 and 3: 1; and sixthly, purifying and separating the 3 rd fraction in the 3 obtained fractions by high performance liquid chromatography gradient elution, collecting the eluate, and obtaining 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabromide B) at the 27.0 th minute.
Example 4: as an optimization of the above example, in the first step, 8ml to 10ml of ethanol was added per 1g of Nepeta cataria.
Example 5: as an optimization of the above embodiment, in the sixth step, the eluent for gradient elution by high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
example 6: the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methylenephenanthrene-1-carbaldehyde (nepetabutyrate B) is applied to the preparation of medicines for preventing inflammation and inhibiting bacteria.
Example 7: the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) is applied to the preparation of anti-inflammatory and antibacterial drugs.
Example 8: the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methylenephenanthrene-1-carbaldehyde (nepetabutyrate B) is applied to the preparation of health products for preventing and treating inflammation and inhibiting bacteria.
Example 9: the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) is obtained by the following method: crushing the schizonepeta bracteata, adding ethanol, soaking for 3 hours at room temperature, heating and refluxing for 3 times and 2 hours each time at 50 ℃, combining reflux extracting solutions each time, and performing reduced pressure recovery and concentration to obtain a schizonepeta bracteatum total extract; secondly, dispersing the schizonepeta tenuifolia total extract by using water, and sequentially extracting by using petroleum ether and dichloromethane to obtain a petroleum ether part and a dichloromethane part; and step three, performing gradient elution and separation on the extract at the petroleum ether part by using a silica gel column chromatography to obtain 8 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1: 0; and fourthly, performing gradient elution separation on the 6 th fraction in the obtained 8 fractions by using a silica gel column chromatography to obtain 5 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 20:1, 10:1 and 3: 1. 1:1, 0: 1; and fifthly, performing gradient elution separation on the 3 rd fraction in the obtained 5 fractions by using a silica gel column chromatography to obtain 3 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10:1, 5:1 and 3: 1; and sixthly, purifying and separating the 3 rd fraction in the 3 obtained fractions by high performance liquid chromatography gradient elution, collecting the eluate, and obtaining 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabromide B) at the 27.0 th minute.
In-vitro anti-inflammatory and antibacterial pharmacodynamic experiments are carried out on the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxyantrhine-1-carbaldehyde (nepetabutyrate B) obtained in the example 9 of the invention, and the MTT colorimetric method is utilized in the in-vitro anti-inflammatory and antibacterial pharmacodynamic experiments.
1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1,4a-dimethyl phenanthrene-1-carbaldehyde (nebetabutyrate B) is taken as an experimental group, aspirin (aspirin) is taken as a control group, a blank group is simultaneously set, RAW 264.7 cells are selected as experimental objects in the experimental group, the control group and the blank group, and after the culture medium is diluted, 6 x 10 cells are taken as the experimental objects4The density of each group is inoculated in a 96-well plate, each well is 100 mu l, after the group is normally cultured in an incubator for 24 hours, the corresponding drugs are added into each group, the final concentration of each group of drugs is respectively 2.5 mu g/ml (1 group), 5 mu g/ml (2 group), 10 mu g/ml (3 group), 20 mu g/ml (4 group) and 40 mu g/ml (5 group), 5 concentrations are set, and each concentration is 3 multiple wells; after 48 hours of incubation, 10. mu.l of MTT was added to each well for staining; continuously culturing for four hours, removing the stock culture solution, adding DMSO 150 μ l into each well, placing on a shaking table, shaking at low speed for 10min to dissolve the crystal completely, detecting optical density value at 570nm wavelength of enzyme-linked immunosorbent assay, and calculating 50% Inhibitory Concentration (IC) according to the optical density value50μ M), optical density value calculation IC50The calculation method of (2) is a prior known technology. IC of experiment group and control group on RAW 264.7 cell50As shown in table 2. The data in table 2 show that 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) has a certain inhibitory effect on RAW 264.7 cells.
1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxyphene-1-carbaldehyde (nepetalate B) is used as an experimental group, Penicillin (amoxicillin and antibacterial drug) is used as a control group, a blank group is simultaneously set, staphylococcus aureus and escherichia coli are selected as experimental objects in the experimental group, a sample is diluted by sterile water or DMSO for a certain time, 100 mu L of the sample is centrifugally taken and added into a hole of an indicator plate to be used as an antibacterial experimental hole, a freshly cultured indicator strain is taken, the concentration of a bacterial suspension is adjusted to 0.5McFarland uniformly coated on the plate, the plate is placed at a corresponding temperature for culturing for 24 hours or 48 hours, and the colony growth condition of each plate is observed. 100 μ L of fresh medium was added to the wells as a negative control well and amoxicillin solution as a positive control. After dilution of the medium, the medium was diluted at 6X 104The cells were inoculated in 96-well plates at a density of 100. mu.l/well and were normal in an incubatorAfter 24 hours of culture, the corresponding drugs are added into each group, so that the final concentration of the drugs in each group is 2.5 mu g/ml (1 group), 5 mu g/ml (2 groups), 10 mu g/ml (3 groups), 20 mu g/ml (4 groups) and 40 mu g/ml (5 groups), and 5 concentrations are set in total, wherein each concentration is 3 multiple wells; after 48 hours of incubation, 10. mu.l of MTT was added to each well for staining; continuously culturing for four hours, removing the stock culture solution, adding DMSO 150 μ l into each well, placing on a shaking table, shaking at low speed for 10min to dissolve the crystal completely, detecting optical density value at 570nm wavelength of enzyme-linked immunosorbent assay, and calculating 50% Inhibitory Concentration (IC) according to the optical density value50μ M), optical density value calculation IC50The calculation method of (2) is a prior known technology. IC of experiment group, control group for staphylococcus aureus and escherichia coli50As shown in table 3. The data in table 3 show that 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (piperidine B) has certain inhibitory effect on staphylococcus aureus and escherichia coli.
In conclusion, the invention discloses a compound 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxyphene-1-carbaldehyde (nebetabutyrate B) for the first time, and the compound is subjected to in vitro anti-inflammatory and antibacterial pharmacodynamic experiments, and the experiments show that the compound has stronger inhibition effect on RAW 264.7 cells, staphylococcus aureus and escherichia coli, so that the compound can be used for preparing anti-inflammatory and antibacterial drugs or/and preparing anti-inflammatory and antibacterial health-care products.
The technical characteristics form an embodiment of the invention, which has strong adaptability and implementation effect, and unnecessary technical characteristics can be increased or decreased according to actual needs to meet the requirements of different situations.
TABLE 1
TABLE 2
TABLE 3
Claims (10)
1. A1, 2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate B) is characterized in that the chemical structural formula is shown as
2. The 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) according to claim 1, which is prepared by the following method: crushing the schizonepeta bracteata, adding ethanol, soaking for 3-4 hours at room temperature, heating and refluxing for 3 times at 50-60 ℃, extracting for 1-3 hours each time, combining the refluxing extracting solutions each time, and recovering and concentrating under reduced pressure to obtain a schizonepeta bracteatum total extract; secondly, dispersing the schizonepeta tenuifolia total extract by using water, and sequentially extracting by using petroleum ether and dichloromethane to obtain a petroleum ether part and a dichloromethane part; and step three, performing gradient elution and separation on the extract at the petroleum ether part by using a silica gel column chromatography to obtain 8 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1: 0; and fourthly, performing gradient elution separation on the 6 th fraction in the obtained 8 fractions by using a silica gel column chromatography to obtain 5 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 20:1, 10:1 and 3: 1. 1:1, 0: 1; and fifthly, performing gradient elution separation on the 3 rd fraction in the obtained 5 fractions by using a silica gel column chromatography to obtain 3 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10:1, 5:1 and 3: 1; and sixthly, purifying and separating the 3 rd fraction in the 3 obtained fractions by high performance liquid chromatography gradient elution, collecting the eluate, and obtaining 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabromide B) at the 27.0 th minute.
3. The 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxyphene-1-carbaldehyde (nepetabutyrate b) according to claim 2, wherein in the first step, 8ml to 10ml of ethanol is added per 1g of nepeta cataria.
4. The 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) according to claim 2 or 3, wherein the eluent for gradient elution by high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
5. a method for preparing 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-methyleneanthrene-1-carbaldehyde (nepetabutyrate b) according to claim 1, comprising the steps of: crushing the schizonepeta bracteata, adding ethanol, soaking for 3-4 hours at room temperature, heating and refluxing for 3 times at 50-60 ℃, extracting for 1-3 hours each time, combining the refluxing extracting solutions each time, and recovering and concentrating under reduced pressure to obtain a schizonepeta bracteatum total extract; secondly, dispersing the schizonepeta tenuifolia total extract by using water, and sequentially extracting by using petroleum ether and dichloromethane to obtain a petroleum ether part and a dichloromethane part; and step three, performing gradient elution and separation on the extract at the petroleum ether part by using a silica gel column chromatography to obtain 8 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1: 0; and fourthly, performing gradient elution separation on the 6 th fraction in the obtained 8 fractions by using a silica gel column chromatography to obtain 5 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 20:1, 10:1 and 3: 1. 1:1, 0: 1; and fifthly, performing gradient elution separation on the 3 rd fraction in the obtained 5 fractions by using a silica gel column chromatography to obtain 3 fractions, wherein the gradient eluent of the silica gel column chromatography comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10:1, 5:1 and 3: 1; and sixthly, purifying and separating the 3 rd fraction in the 3 obtained fractions by high performance liquid chromatography gradient elution, collecting the eluate, and obtaining 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabromide B) at the 27.0 th minute.
6. The method for producing 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) according to claim 5, wherein in the first step, 8ml to 10ml of ethanol is added per 1g of nepeta cataria.
7. The method for preparing 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) according to claim 5 or 6, wherein the eluent for gradient elution by high performance liquid chromatography is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85: 15.
8. use of the 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) according to claim 1,2,3 or 4 for the preparation of a medicament for preventing inflammation and inhibiting bacteria.
9. Use of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) according to claim 1,2,3 or 4 for the preparation of anti-inflammatory and antibacterial medicaments.
10. The use of 1,2,3,4,4a,9,10,10 a-octahydro-2-hydroxy-7-isoproyl-1, 4 a-dimethoxybenzene-1-carbaldehyde (nepetabutyrate B) as claimed in claim 1,2,3 or 4 in the preparation of health products for preventing and treating inflammation and inhibiting bacteria.
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