CN113861008B - Large bud rosin diterpene, preparation method thereof and application thereof in preparation of anti-inflammatory and antibacterial drugs for preventing or/and treating inflammation - Google Patents
Large bud rosin diterpene, preparation method thereof and application thereof in preparation of anti-inflammatory and antibacterial drugs for preventing or/and treating inflammation Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 206010061218 Inflammation Diseases 0.000 title claims abstract description 11
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- 229940124599 anti-inflammatory drug Drugs 0.000 title abstract description 10
- 229940124350 antibacterial drug Drugs 0.000 title abstract description 9
- 150000004141 diterpene derivatives Chemical class 0.000 title abstract description 6
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- 241000951473 Schizonepeta Species 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 241000191967 Staphylococcus aureus Species 0.000 claims abstract description 8
- 238000000926 separation method Methods 0.000 claims abstract description 8
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- 230000005764 inhibitory process Effects 0.000 claims abstract description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 84
- 239000003208 petroleum Substances 0.000 claims description 54
- 238000010828 elution Methods 0.000 claims description 40
- 238000010898 silica gel chromatography Methods 0.000 claims description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
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- 125000001033 ether group Chemical group 0.000 claims description 12
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 10
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- 239000003814 drug Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
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- 239000003480 eluent Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 2
- 229960003022 amoxicillin Drugs 0.000 description 2
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- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- -1 terpenoid compounds Chemical class 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
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- 241001529733 Nepeta Species 0.000 description 1
- 241001612423 Nepeta bracteata Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- 230000035619 diuresis Effects 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
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Classifications
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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
-
- 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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- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to the technical field of separation and purification of schizonepeta makino, in particular to a rosin diterpene with a large bract, a preparation method thereof and application thereof in preparing anti-inflammatory and antibacterial drugs for preventing or/and treating inflammation. The invention discloses a compound 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isophthaloyl-1, 4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) for the first time, and in-vitro anti-inflammatory and antibacterial pharmacodynamics experiments are carried out on the compound, the experiment shows 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 antibacterial.
Description
Technical Field
The invention relates to the technical field of separation and purification of schizonepeta majora, in particular to a rosin diterpene with 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthene-1-carbaldehyde (nepetabrate B), a preparation method thereof and application thereof in preparing anti-inflammatory and antibacterial drugs for preventing or/and treating inflammation.
Background
Herba Schizonepetae Nepeta bracteata Benth is a Nepeta plant of Labiatae, and is mainly distributed in the countries such as Pakistan, nepal, iran, etc., with Uygur name of "Zaofa", which is commonly known as Shenxiang herb, and has wide clinical application, mainly imported. The whole herb is used as a medicine, has faint scent of qi, light taste and slight dampness, enters lung and liver channels, has the effects of relieving cough and asthma, clearing heat and promoting diuresis, and is clinically used for treating symptoms such as tracheitis, cough and asthma, cold and fever, difficult urination and the like. In addition, the schizonepeta herb has the characteristics of easy source, low cost, reliable clinical curative effect, small toxic and side effects and the like. So far, the focus of research on schizonepeta makino and basic theoretical research are not seen, modern pharmacology shows that the extract has remarkable anti-inflammatory and antibacterial activities, but related research on chemical components is not carried out yet, and the schizonepeta makino is a species which can treat respiratory diseases well, so that the schizonepeta makino has been paid attention to in recent years.
The drug effect of the schizonepeta majora is mainly derived from terpenoid compounds, including monoterpenes and diterpenoid compounds, wherein the diterpenoid components of the dominant component have good anti-inflammatory and antibacterial activities, so that the diterpenoid monomer compounds of the schizonepeta majora are developed and utilized, the potential medicinal value of the schizonepeta majora is further excavated, the structure and physical and chemical properties of the monomer compounds of the schizonepeta majora are determined and characterized, and the schizonepeta majora has important significance in development and utilization of the schizonepeta majora.
Disclosure of Invention
The invention provides 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isophthalene-1, 4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) and a preparation method and application thereof, overcomes the defects of the prior art, and firstly discloses 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isophthalamide-1, 4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) and application thereof in preparing anti-inflammatory and antibacterial drugs or/and preparing anti-inflammatory and antibacterial health care products.
One of the technical schemes of the invention is realized by the following measures: 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B), with chemical structural formula of
The following are further optimizations and/or improvements to one of the above-described inventive solutions:
the preparation method comprises the following steps: crushing schizonepeta makino, adding ethanol, soaking for 3-4 hours at room temperature, heating and reflux-extracting for 3 times at 50-60 ℃ for 1-3 hours each time, combining the reflux extracting solutions each time, decompressing and recovering and concentrating to obtain schizonepeta makino total extractum; dispersing the total extract of schizonepeta makino with water, and extracting with petroleum ether and dichloromethane in sequence to obtain a petroleum ether part and a dichloromethane part; step three, taking petroleum ether part extractum, and obtaining 8 fractions after gradient elution and separation by a silica gel column chromatography, wherein the gradient elution liquid 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 sequentially 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1:1, 1:0; fourthly, separating the 6 th fraction in the 8 fractions by silica gel column chromatography gradient elution to obtain 5 fractions, wherein the silica gel column chromatography gradient elution 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; fifthly, separating the 3 rd fraction in the 5 fractions by silica gel column chromatography gradient elution to obtain 3 fractions, wherein the silica gel column chromatography gradient elution 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, a step of; and sixthly, eluting, purifying and separating the 3 rd fraction in the 3 obtained fractions by a high performance liquid chromatography gradient, collecting the eluate, and obtaining 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthine-1-carbaldehyde (nepetabrate B) at the 27.0 min.
In the first step, 8ml to 10ml of ethanol is added to each 1g of schizonepeta.
In the sixth step, the eluent of the high performance liquid chromatography gradient elution is a mixed solution of methanol and water, wherein the volume ratio of the methanol to the water is 85:15.
the second technical scheme of the invention is realized by the following measures: a preparation method of 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthene-1-carbaldehyde (nepetabrate B) is carried out according to the following steps: crushing schizonepeta makino, adding ethanol, soaking for 3-4 hours at room temperature, heating and reflux-extracting for 3 times at 50-60 ℃ for 1-3 hours each time, combining the reflux extracting solutions each time, decompressing and recovering and concentrating to obtain schizonepeta makino total extractum; dispersing the total extract of schizonepeta makino with water, and extracting with petroleum ether and dichloromethane in sequence to obtain a petroleum ether part and a dichloromethane part; step three, taking petroleum ether part extractum, and obtaining 8 fractions after gradient elution and separation by a silica gel column chromatography, wherein the gradient elution liquid 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 sequentially 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1:1, 1:0; fourthly, separating the 6 th fraction in the 8 fractions by silica gel column chromatography gradient elution to obtain 5 fractions, wherein the silica gel column chromatography gradient elution 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; fifthly, separating the 3 rd fraction in the 5 fractions by silica gel column chromatography gradient elution to obtain 3 fractions, wherein the silica gel column chromatography gradient elution 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, a step of; and sixthly, eluting, purifying and separating the 3 rd fraction in the 3 obtained fractions by a high performance liquid chromatography gradient, collecting the eluate, and obtaining 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthine-1-carbaldehyde (nepetabrate B) at the 27.0 min.
The following is a further optimization and/or improvement of the second technical scheme of the invention:
in the first step, 8ml to 10ml of ethanol is added to each 1g of schizonepeta.
In the sixth step, the eluent of the high performance liquid chromatography gradient elution is a mixed solution of methanol and water, wherein the volume ratio of the methanol to the water is 85:15.
the third technical scheme of the invention is realized by the following measures: application of 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) in preparing medicines for preventing inflammation and inhibiting bacteria.
The fourth technical scheme of the invention is realized by the following measures: use of 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) for the preparation of an anti-inflammatory and antibacterial agent.
The fifth technical scheme of the invention is realized by the following measures: 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) is used for preparing health care products for preventing and treating inflammation and inhibiting bacteria.
The invention discloses a compound 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isophthaloyl-1, 4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) for the first time, and experiments on in vitro anti-inflammatory and antibacterial pharmacodynamics are carried out on the compound, so that the compound has strong inhibition effect on RAW 264.7 cells, staphylococcus aureus and escherichia coli, and can be used for preparing anti-inflammatory and antibacterial drugs or/and antibacterial health care products.
Drawings
FIG. 1 is a chemical structure of 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthene-1-carbaldehyde (nepetabrate B) according to the present invention.
FIG. 2 is a schematic diagram of 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthene-1-carbaldehyde (nepetabrate B) according to the present invention 1 H-NMR spectrum.
FIG. 3 is a schematic diagram of 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthene-1-carbaldehyde (nepetabrate B) according to the present invention 13 C-APT spectrogram.
Detailed Description
The present invention is not limited by the following examples, and specific embodiments can be determined according to the technical scheme and practical situations of the present invention. The various chemical reagents and chemical supplies mentioned in the invention are all commonly known and used in the prior art unless specified otherwise; the percentages in the invention are mass percentages unless specified otherwise; the solutions in the invention are aqueous solutions in which the solvent is water unless otherwise specified, for example, the hydrochloric acid solution is hydrochloric acid aqueous solution; the room temperature and the room temperature in the present invention generally refer to temperatures ranging from 15 ℃ to 25 ℃, and are generally defined as 25 ℃.
The invention is further described below with reference to examples:
example 1: the 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyyl-1, 4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) is characterized by the chemical structural formula
Subjecting 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyyl-1, 4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) of example 1 of the present invention to nuclear magnetic resonance hydrogen spectrometry 1 H-NMR) and nuclear magnetic resonance carbon spectrum 13 C-APT).
1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthene-1-carbaldehyde (nepetabrate B) described in this example 1 The H-NMR spectrum is shown in FIG. 2.
The 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthene-1-carbaldehyde (nepetabrate B) described in this example 13 The C-APT spectrum is shown in FIG. 3.
The pattern analysis is carried out on the graphs of the figures 2 and 3, and the peaks of the figures 2 and 3 are attributed to each other, so that the chemical shift and the peak type of carbon and hydrogen in the structure of the compound 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenate-1-carbaldehyde (nepetabrate B) are obtained, and the chemical structural formula of the compound is shown in the figure 1. Wherein, each peak assignment of fig. 2 and 3 is shown in table 1.
Example 2: the 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) is prepared according to the following method: crushing schizonepeta makino, adding ethanol, soaking for 3-4 hours at room temperature, heating and reflux-extracting for 3 times at 50-60 ℃ for 1-3 hours each time, combining the reflux extracting solutions each time, decompressing and recovering and concentrating to obtain schizonepeta makino total extractum; dispersing the total extract of schizonepeta makino with water, and extracting with petroleum ether and dichloromethane in sequence to obtain a petroleum ether part and a dichloromethane part; step three, taking petroleum ether part extractum, and obtaining 8 fractions after gradient elution and separation by a silica gel column chromatography, wherein the gradient elution liquid 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 sequentially 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1:1, 1:0; fourthly, separating the 6 th fraction in the 8 fractions by silica gel column chromatography gradient elution to obtain 5 fractions, wherein the silica gel column chromatography gradient elution 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; fifthly, separating the 3 rd fraction in the 5 fractions by silica gel column chromatography gradient elution to obtain 3 fractions, wherein the silica gel column chromatography gradient elution 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, a step of; and sixthly, eluting, purifying and separating the 3 rd fraction in the 3 obtained fractions by a high performance liquid chromatography gradient, collecting the eluate, and obtaining 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthine-1-carbaldehyde (nepetabrate B) at the 27.0 min.
Example 3: as an optimization of the above examples, the 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) was prepared as follows: firstly, crushing schizonepeta makino, adding ethanol, soaking for 3 hours or 4 hours at room temperature, heating and reflux-extracting for 3 times at 50 ℃ or 60 ℃ for 1 hour or 3 hours each time, combining reflux extracting solutions each time, decompressing and recovering and concentrating to obtain schizonepeta makino total extractum; dispersing the total extract of schizonepeta makino with water, and extracting with petroleum ether and dichloromethane in sequence to obtain a petroleum ether part and a dichloromethane part; step three, taking petroleum ether part extractum, and obtaining 8 fractions after gradient elution and separation by a silica gel column chromatography, wherein the gradient elution liquid 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 sequentially 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1:1, 1:0; fourthly, separating the 6 th fraction in the 8 fractions by silica gel column chromatography gradient elution to obtain 5 fractions, wherein the silica gel column chromatography gradient elution 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; fifthly, separating the 3 rd fraction in the 5 fractions by silica gel column chromatography gradient elution to obtain 3 fractions, wherein the silica gel column chromatography gradient elution 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, a step of; and sixthly, eluting, purifying and separating the 3 rd fraction in the 3 obtained fractions by a high performance liquid chromatography gradient, collecting the eluate, and obtaining 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthine-1-carbaldehyde (nepetabrate B) at the 27.0 min.
Example 4: as an optimization of the above examples, in the first step, 8ml to 10ml of ethanol was added per 1g of schizonepeta makino.
Example 5: as an optimization of the above embodiment, in the sixth step, the eluent of the high performance liquid chromatography gradient elution is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85:15.
example 6: the application of the 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) in preparing medicaments for preventing inflammation and inhibiting bacteria.
Example 7: the 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) is used for preparing anti-inflammatory and antibacterial drugs.
Example 8: the 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) is used for preparing health care products for preventing and treating inflammation and inhibiting bacteria.
Example 9: the 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) is obtained according to the following method: crushing schizonepeta makino, adding ethanol, soaking for 3 hours at room temperature, heating and reflux-extracting for 3 times at 50 ℃ for 2 hours each time, combining the reflux extracting solutions each time, decompressing and recovering and concentrating to obtain schizonepeta makino total extractum; dispersing the total extract of schizonepeta makino with water, and extracting with petroleum ether and dichloromethane in sequence to obtain a petroleum ether part and a dichloromethane part; step three, taking petroleum ether part extractum, and obtaining 8 fractions after gradient elution and separation by a silica gel column chromatography, wherein the gradient elution liquid 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 sequentially 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1:1, 1:0; fourthly, separating the 6 th fraction in the 8 fractions by silica gel column chromatography gradient elution to obtain 5 fractions, wherein the silica gel column chromatography gradient elution 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; fifthly, separating the 3 rd fraction in the 5 fractions by silica gel column chromatography gradient elution to obtain 3 fractions, wherein the silica gel column chromatography gradient elution 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, a step of; and sixthly, eluting, purifying and separating the 3 rd fraction in the 3 obtained fractions by a high performance liquid chromatography gradient, collecting the eluate, and obtaining 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthine-1-carbaldehyde (nepetabrate B) at the 27.0 min.
The 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isophthaloyl-1, 4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) obtained in example 9 of the present invention was subjected to in vitro anti-inflammatory and antibacterial pharmacodynamic experiments, which utilized MTT colorimetric method.
Taking 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) as experimental group, aspin (aspirin, anti-inflammatory drug) as control group, setting blank group at the same time, selecting RAW 264.7 cells as experimental group, control group and blank group, taking 6×10 after dilution of culture medium 4 The density of each ml is inoculated in a 96-well plate, 100 mu l of each well is cultured normally in an incubator for 24 hours, and the corresponding medicines are added into each group, so that the final concentration of each group of medicines 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 3 compound wells are arranged for each concentration; after 48 hours of incubation, 10. Mu.l of MTT was added to each well for staining; after further culturing for four hours, the stock culture was aspirated, 150. Mu.l of DMSO was added to each well,placing on a shaking table, oscillating at low speed for 10min to dissolve the crystal, detecting optical density value at 570nm wavelength of ELISA, and calculating 50% Inhibition Concentration (IC) according to the optical density value 50 Mu M), optical density value calculating IC 50 The calculation method is a prior known technology. IC of experimental group and control group on RAW 264.7 cells 50 As shown in table 2. As can be seen from the data in Table 2, 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4 a-dimethylphenanthene-1-carbaldehyde (nepetabrate B) of the present invention has a certain inhibition effect on RAW 264.7 cells.
Taking 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) as an experimental group, taking Penicillin (amoxicillin) as a control group, simultaneously setting a blank group, taking staphylococcus aureus and escherichia coli as experimental objects in the experimental group, diluting a sample by a certain multiple with sterile water or DMSO, centrifuging to take 100 mu L of the sample, adding the sample into a hole of an indicator bacteria plate to serve as a bacteriostasis experimental hole, taking a freshly cultured indicator strain, regulating the concentration of a bacterial suspension to 0.5McFarland, uniformly coating the bacterial suspension on the plate, placing the bacterial suspension on the flat plate for culturing for 24 hours or 48 hours at a corresponding temperature, and observing the colony growth condition of each dish. 100 μl of fresh medium was added to the wells as negative control wells and amoxicillin solution as positive control. After dilution of the medium, the culture medium was diluted to 6X 10 4 The density of each ml is inoculated in a 96-well plate, 100 mu l of each well is cultured normally in an incubator for 24 hours, and the corresponding medicines are added into each group, so that the final concentration of each group of medicines 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 3 compound wells are arranged for each concentration; after 48 hours of incubation, 10. Mu.l of MTT was added to each well for staining; after further culturing for four hours, the stock culture was aspirated, 150. Mu.l of DMSO was added to each well, the mixture was allowed to oscillate on a shaking table at low speed for 10min to allow the crystals to be sufficiently dissolved, and the optical density value was measured at 570nm wavelength of an ELISA, and 50% Inhibitory Concentration (IC) was calculated from the optical density value 50 Mu M), optical density value calculating IC 50 The calculation method is a prior known technology. Experiment group, control group against staphylococcus aureus and escherichia coliIC 50 As shown in table 3. As can be seen from the data in Table 3, 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) disclosed by the invention has a certain inhibition effect on staphylococcus aureus and escherichia coli.
In summary, the invention discloses the compounds 1,2,3, 4a,9,10 a-octahydro-2-hydroxy-7-isopropyl-1,4a-dimethylphenanthrene-1-carbaldehyde (nepetabrate B) for the first time, and the compounds are subjected to in vitro anti-inflammatory and antibacterial pharmacodynamic experiments, so that the experiments show that the compounds have strong inhibition effects on RAW 264.7 cells, staphylococcus aureus and escherichia coli, and the compounds can be used for preparing anti-inflammatory and antibacterial drugs or/and preparing anti-inflammatory and antibacterial health care products.
The technical characteristics form the embodiment of the invention, have stronger adaptability and implementation effect, and can increase or decrease unnecessary technical characteristics according to actual needs so as to meet the requirements of different situations.
TABLE 1
TABLE 2
TABLE 3 Table 3
Claims (6)
1. A compound is characterized by having a chemical structural formula of
。
2. A process for the preparation of a compound according to claim 1, characterized by the following steps: crushing schizonepeta makino, adding ethanol, soaking for 3-4 hours at room temperature, heating and reflux-extracting for 3 times at 50-60 ℃ for 1-3 hours each time, combining the reflux extracting solutions each time, decompressing and recovering and concentrating to obtain schizonepeta makino total extractum; dispersing the total extract of schizonepeta makino with water, and extracting with petroleum ether and dichloromethane in sequence to obtain a petroleum ether part and a dichloromethane part; step three, taking petroleum ether part extractum, and obtaining 8 fractions after gradient elution and separation by a silica gel column chromatography, wherein the gradient elution liquid 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 sequentially 1:0, 100:1 and 50: 1. 25:1, 8:1, 5:1, 1:1, 1:0; fourthly, separating the 6 th fraction in the 8 fractions by silica gel column chromatography gradient elution to obtain 5 fractions, wherein the silica gel column chromatography gradient elution 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; fifthly, separating the 3 rd fraction in the 5 fractions by silica gel column chromatography gradient elution to obtain 3 fractions, wherein the silica gel column chromatography gradient elution 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, a step of; and sixthly, eluting, purifying and separating the 3 rd fraction in the 3 obtained fractions by using a high performance liquid chromatography gradient, collecting the eluate, and obtaining the compound at the 27.0 th minute.
3. The method for producing a compound according to claim 2, wherein in the first step, 8ml to 10ml ethanol is added per 1. 1g bud schizonepeta.
4. A method for preparing a compound according to claim 2 or 3, wherein in the sixth step, the eluent of the high performance liquid chromatography gradient elution is a mixed solution of methanol and water, wherein the volume ratio of methanol to water is 85:15.
5. use of a compound according to claim 1 for the preparation of a medicament for the prophylaxis of inflammation of RAW 264.7 cells and for the inhibition of staphylococcus aureus and escherichia coli.
6. Use of a compound according to claim 1 for the preparation of a medicament against RAW 264.7 cell inflammation and against staphylococcus aureus and escherichia coli.
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