CN115636801B - Amide alkaloid and preparation method and application thereof - Google Patents
Amide alkaloid and preparation method and application thereof Download PDFInfo
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- 229930013930 alkaloid Natural products 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
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- 150000001875 compounds Chemical class 0.000 claims description 21
- 235000019510 Long pepper Nutrition 0.000 claims description 8
- 240000003455 Piper longum Species 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000499 gel Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
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- 239000006210 lotion Substances 0.000 claims description 2
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- 239000006187 pill Substances 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
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- 210000004027 cell Anatomy 0.000 description 4
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- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
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- 206010002383 Angina Pectoris Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
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- 231100000002 MTT assay Toxicity 0.000 description 1
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- 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
- 241000722363 Piper Species 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
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- 229940125904 compound 1 Drugs 0.000 description 1
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- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
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- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
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- 210000002540 macrophage Anatomy 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 235000017807 phytochemicals Nutrition 0.000 description 1
- 229930000223 plant secondary metabolite Natural products 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Abstract
The invention provides an amide alkaloid and a preparation method and application thereof, wherein the structure of the amide alkaloid is selected from one of the following structures:the invention also provides a preparation method of the amide alkaloid compound, which is simple and easy to operate, and the invention further provides application of the amide alkaloid compound in preparing anti-inflammatory drugs.
Description
Technical Field
The invention relates to the technical field of medicines, in particular to an amide alkaloid obtained by separating and purifying from long pepper roots, a preparation method thereof and application thereof in preparing anti-inflammatory medicines.
Background
Fructus Piperis Longi (Piperlongum L.) is a climbing vine of Piper genus (Piperceae), mainly produced in Vietnam, philippine and Indonesia, and cultivated in regions such as Guangdong, guangxi and Fujian. The mature fruit cluster of the long pepper is a traditional Chinese medicine, has the effects of warming the middle-jiao, dispelling cold, descending qi and relieving pain, and is commonly used for treating diseases such as epigastric and abdominal crymodynia, vomit, headache, toothache, angina pectoris, coronary heart disease and the like. The phytochemicals contain amides, sterols, terpenes, lignans, etc. While the chemical composition of its roots is rarely studied. The novel compound with activity is found from the root, and has important significance for resource utilization and development.
The occurrence and development of many diseases are closely related to inflammation. Inflammation is also one of the common symptoms of many skin disorders. Skin is an important barrier for the human body. Inflammation can make the skin fragile and sensitive, so that the skin is more easily stimulated by external sources, and inflammatory factors are more active. The heavier the inflammation, the more fragile the skin, forming a vicious circle. Psoriasis, systemic lupus erythematosus, atopic rhinitis, seborrheic dermatitis are all relatively common chronic inflammatory skin diseases. Pneumonia/hepatitis, tumor, cardiovascular diseases, rheumatism, diabetes and other diseases are also closely related to inflammation.
Therefore, it is important to find new compounds having anti-inflammatory activity for disease prevention and treatment.
Disclosure of Invention
The present invention aims to solve at least one of the technical problems existing in the prior art to a certain extent, and therefore, in a first aspect of the present invention, an amide alkaloid is provided, wherein the structure of the amide alkaloid is selected from one of the following structures:
in a second aspect of the present invention, the present invention also provides a method for preparing the amide alkaloid provided in the first aspect of the present invention, wherein the amide alkaloid is obtained by extraction and separation of long pepper root.
In one or more embodiments of the present invention, the preparation method of the amide alkaloid includes the following steps:
(1) pulverizing fructus Piperis Longi root, extracting with first organic solvent, and concentrating the extractive solution to obtain extract;
(2) separating the extract obtained in the step (1) by column chromatography to obtain a coarse fraction;
(3) and (3) separating the crude fraction obtained in the step (2) through column chromatography to obtain the amide alkaloid.
In one or more embodiments of the present invention, in the step (1), the first organic solvent is ethanol or methanol.
In one or more embodiments of the present invention, in the step (2), the column chromatography is macroporous resin or macroporous resin.
In one or more embodiments of the present invention, in the step (3), the column chromatography is selected from at least one of silica gel column chromatography, small pore resin, reverse phase silica gel column chromatography, and high performance liquid preparation chromatography.
In one or more embodiments of the invention, the column chromatography separation is performed with a second solvent selected from at least two of water, methanol, acetonitrile, acetone, ethyl acetate, petroleum ether, dichloromethane, and isopropanol.
In a third aspect of the present invention, the present invention also provides an application of the amide alkaloid in the first aspect of the present invention in preparing an anti-inflammatory drug.
In a fourth aspect of the present invention, there is also provided a pharmaceutical formulation comprising at least one of compounds 1, 2, 3, 4, 5, the structural formula of compounds 1, 2, 3, 4, 5 being as follows:
in one or more embodiments of the invention, the pharmaceutical formulation is a paste, film, lotion, tincture, gel, aerosol, pill, capsule, tablet or granule.
The invention has the beneficial effects that:
the invention provides a novel amide alkaloid compound which has medicinal value, and also provides a preparation method of the amide alkaloid compound, which is simple and easy to operate, and the invention further provides application of the amide alkaloid compound in preparing anti-inflammatory drugs.
Drawings
FIG. 1 is a flow chart of the separation and preparation of compounds 1-5 in Piper longum roots.
Detailed Description
The invention is further described below in conjunction with the specific examples and figures, which are provided to illustrate the invention and should not be construed to limit the scope of the invention. The following examples are conducted under conventional conditions or conditions recommended by the manufacturer, and the methods used are conventional methods known in the art, and the consumables and reagents used are commercially available unless otherwise specified. Unless otherwise defined, the technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. In addition, any method or material similar or equivalent to those described may be used in the present invention.
Example 1: isolated preparation of Compounds 1-5
FIG. 1 is a flow chart of the separation and preparation of compounds 1-5 in Piper longum roots, comprising the following steps:
dried Piper longum roots (5.4 kg) were crushed and soaked with 25.0L of 95% (volume fraction) ethanol at room temperature for 3 times, each for 5 days. The filtrates obtained after filtration were combined and concentrated under reduced pressure to finally obtain 260g of extract. Coarse separation of the extract with macroporous resin, eluting with methanol-water as eluent with four polarities of 40% (volume fraction), 60% (volume fraction), 75% (volume fraction) and 90% (volume fraction) methanol, respectively, combining according to TLC plate condition, and separating the extract into 4 components (Fr.1-Fr.4).
Separating the Fr.2 part by a silica gel column, wherein the elution system is petroleum ether: ethyl acetate (volume ratio 8:1-1:1), ethyl acetate: methanol (volume ratio 1:1) and methanol, the fr.2 fraction was separated into 8 fractions (fr 2.1-fr 2.8) by TLC plate combining. The fraction Fr2.5 was first separated using a gel column, and the fractions were separated into 8 components after spot-plating (Fr2.5.1-Fr2.5.8). The Fr2.5.3 fraction was subjected to ODS and silica gel column separation to obtain Compound 1.
The fraction Fr2.6 was first separated using a gel column, combined by TLC plate and separated into 7 fractions (Fr 2.6.1-Fr 2.6.7). Further separation of the Fr2.6.2 fraction by ODS, silica gel column (Petroleum ether: ethyl acetate (volume ratio 1:1)) and HPLC (40% volume fraction acetonitrile) gives compounds 2-5.
Example 2: the structure of compounds 1-5 was determined.
The structure of the compounds 1-5 is determined by data analysis such as high resolution mass spectrum, ultraviolet spectrum, infrared spectrum, nuclear magnetic resonance spectrum and the like. Table 1 shows the hydrogen and carbon spectrum data for Compound 1, and Table 2 shows the hydrogen spectrum data for Compounds 2-5.
TABLE 1 Compound 1 1 H (400 MHz) NMR and 13 c NMR (100 MHz) data (Recorded in CDCl 3 ,δ:ppm)
TABLE 2 Compounds 2-5 1 H (400 MHz) NMR data (Recorded in CDCl 3 ,δ:ppm)
Example 3: anti-inflammatory Activity test of Compounds 1-5.
Anti-inflammatory assay: compounds 1-5 were evaluated for anti-inflammatory activity using the Griess method. The experimental cells were RAW 264.7 mouse macrophages, and the cells were cultured in DMEM medium (containing 10% FBS, 100IU/mL penicillin, 100. Mu.g/mL streptomycin). The cytotoxicity of the compound against RAW 264.7 was detected in advance by MTT assay, and according to the experimental results, the anti-inflammatory activity was tested in a concentration range where the compound was not toxic to the cells. Cells were treated with different concentrations of compound and LPS solution for 24 hours, and the reacted medium was mixed with Griess reagent and reacted at room temperature for 10 minutes to measure absorbance at 540 nm. The test was set with a blank control group, a model building group, a drug group, and indomethacin as a positive control drug, and each test was repeated 3 times to evaluate the inhibition of Nitric Oxide (NO). The NO inhibition rate is calculated according to the following formula: NO inhibition rate= (a Building module -A Pharmaceutical set )/(A Building module -A Blank group )×100％
The results are shown in Table 3:
TABLE 3 anti-inflammatory Activity of Compounds 1-5
Values are expressed as the mean + -SD (n=3). Indomethacin IC 50 Between 49-56 μm.
While embodiments of the present invention have been shown and described above, it should be understood that the above embodiments are illustrative and not to be construed as limiting the present invention, and that variations, modifications, alternatives and variations of the above embodiments may be made by those skilled in the art within the scope of the present invention and are intended to be included within the scope of the present invention.
Claims (5)
1. An amide alkaloid, characterized in that the structure of the amide alkaloid is selected from one of the following structures:
2. a method for preparing an amide alkaloid according to claim 1, wherein the amide alkaloid is obtained by extraction and separation of long pepper roots;
the preparation method of the amide alkaloid comprises the following steps:
(1) pulverizing fructus Piperis Longi root, extracting with 95% ethanol, and concentrating the extractive solution to obtain extract;
(2) coarsely separating the extract obtained in the step (1) by using macroporous resin;
(3) eluting with methanol-water as eluent to obtain 4 components, and separating Fr.2 part with silica gel column and gel column to obtain compounds 1-5.
3. Use of an amide alkaloid according to claim 1 for the preparation of an anti-inflammatory drug.
4. A pharmaceutical formulation comprising at least one of compounds 1, 2, 3, 4, 5, the structural formula of compounds 1, 2, 3, 4, 5 being as follows:
5. the pharmaceutical formulation of claim 4, wherein the pharmaceutical formulation is a paste, film, lotion, tincture, gel, aerosol, pill, capsule, tablet, or granule.
Priority Applications (1)
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| CN202211316480.3A CN115636801B (en) | 2022-10-26 | 2022-10-26 | Amide alkaloid and preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211316480.3A CN115636801B (en) | 2022-10-26 | 2022-10-26 | Amide alkaloid and preparation method and application thereof |
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| Publication Number | Publication Date |
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| CN115636801A CN115636801A (en) | 2023-01-24 |
| CN115636801B true CN115636801B (en) | 2024-01-09 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009041787A2 (en) * | 2007-09-28 | 2009-04-02 | Korea Research Institute Of Bioscience And Biotechnology | Pharmaceutical composition comprising inhibitors of cell adhesion molecule isolated from piper nigrum for the prevention and treatment of inflammatory disease |
| CN101554409A (en) * | 2008-04-10 | 2009-10-14 | 周亚伟 | Long pepper alkaloid and preparation method, preparation and application thereof |
| CN109350614A (en) * | 2018-12-13 | 2019-02-19 | 中国科学院新疆理化技术研究所 | A kind of hypoglycemic purposes of piperlongumine alkaloid |
| CN111217768A (en) * | 2018-11-23 | 2020-06-02 | 四川大学 | Alkaloid, and extraction method and application from black pepper |
-
2022
- 2022-10-26 CN CN202211316480.3A patent/CN115636801B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009041787A2 (en) * | 2007-09-28 | 2009-04-02 | Korea Research Institute Of Bioscience And Biotechnology | Pharmaceutical composition comprising inhibitors of cell adhesion molecule isolated from piper nigrum for the prevention and treatment of inflammatory disease |
| CN101554409A (en) * | 2008-04-10 | 2009-10-14 | 周亚伟 | Long pepper alkaloid and preparation method, preparation and application thereof |
| CN111217768A (en) * | 2018-11-23 | 2020-06-02 | 四川大学 | Alkaloid, and extraction method and application from black pepper |
| CN109350614A (en) * | 2018-12-13 | 2019-02-19 | 中国科学院新疆理化技术研究所 | A kind of hypoglycemic purposes of piperlongumine alkaloid |
Non-Patent Citations (1)
| Title |
|---|
| Alkaloids from Black Pepper (Piper nigrum L.) Exhibit Anti-In fl ammatory Activity in Murine Macrophages by Inhibiting Activation of NF-κB Pathway;Heying Pei等;J. Agric. Food Chem.;第68卷;2406−2417 * |
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