CN115677732B - Alkaloid dimer and application thereof - Google Patents
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Abstract
The invention discloses an alkaloid dimer and application thereof, wherein the alkaloid dimer is shown in a formula (I) or a formula (II):experiments prove that the alkaloid dimer can obviously inhibit the function of LPS for inducing mouse macrophage RAW264.7 to release NO under the concentration of 5.0-20.0 mu M, wherein the IC of the alkaloid dimer II 50 The value is obviously stronger than that of the indometacin which is a clinically commonly used non-steroidal anti-inflammatory drug; IC of alkaloid dimer I 50 The value is equivalent to the effect of indomethacin. The above results suggest that the alkaloid dimers of the present invention can be used as anti-inflammatory drugs for further development.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to an alkaloid dimer and application thereof.
Background
Nitric Oxide (NO) acts as a cytokine in the organism, as a nerve conduction signal and vasodilation at low concentrations, but as a cytotoxin at high concentrations (E.D. garcin et al, nature Chemical Biology,2008,4,700-707). NO in the organism can catalyze arginine production by Nitric Oxide Synthase (NOs) present in endothelial cells, macrophages, neurophages and nerve cells (D.A.Geller, T.R.Billiar.Cancer and Metastasis Reviews,1998,17,7-23). Nitric oxide synthase includes three types, neuronal nitric oxide synthase (nNOS), endothelial nitric oxide synthase (eNOS), and Inducible Nitric Oxide Synthase (iNOS) that induces expression after injury. Wherein Inducible Nitric Oxide Synthase (iNOS) is expressed under the induction of cytokines or pathogens and induces the production of large amounts of NO. The overproduction of NO in the organism is thought to be associated with diseases such as inflammation, pain, rheumatoid arthritis, inflammatory bowel disease, immune type diabetes, stroke, cancer, thrombosis, and susceptibility to infection (K.Bian, F.Murad.Frontiers in Bioscience,2003,8, d264-d 278). Thus, the development of a drug which inhibits the production of NO by an organism can be one of the effective strategies for developing a drug for treating the above-mentioned related diseases.
The charm of natural products is the diversity and novelty of chemical structure and biological activity, which have been endless sources of inspiration generation and lead discovery by pharmaceutical researchers. The Chinese medicinal herbs Corydalis tuber, also called Corydalis tuber and Corydalis tuber, are dry tubers of Corydalis tuber Corydalis yanhusuo W.T. Wang of Corydalis genus of Papaveraceae family (Papaveraceae), are warm in nature, bitter in taste, and entering heart, spleen, liver and lung meridians, are wonderful products for activating blood circulation to remove blood stasis, promoting qi circulation and relieving pain, so that the effect of relieving pain is known. In recent years, a great deal of research has been conducted on the chemical components of rhizoma corydalis, and it has been found that these components are all typical protoberberine-type, aporphine-type and benzylisoquinoline-type alkaloids (Tang Yifeng. Clinical research in TCM, 2018 (23): 144-146). Whether these components are the effective components of rhizoma corydalis for the traditional efficacy is still to be further studied. With the improvement of separation, purification and structure identification technologies, more and more natural dimer molecules are obtained and identified, and hydrogen bond donors, acceptors and active functional groups are added due to the formation of symmetrical or asymmetrical dimers, so that the binding capacity of the natural dimer molecules with various pharmacologically relevant acceptors is enhanced, and therefore, the natural dimer molecules often show stronger biological activity than haploids. Alkaloid is a major component of natural products, has various structures and outstanding biological activity, and through literature research on natural alkaloid dimers in recent 20 years, 270 natural alkaloid dimers have been reported in total, and most alkaloid dimers show stronger biological activities such as tumor resistance, plasmodium resistance and the like. In addition to the reported typical alkaloid components, whether the novel alkaloid dimer components exist or not is still to be researched, and how the biological activity of the novel alkaloid dimer compounds is not clear, so that the method has high research significance and development value, and can provide scientific basis for further elucidating the pharmacodynamic substance basis of the corydalis tuber and developing novel medicines.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide an alkaloid dimer.
A second object of the present invention is to provide the use of the above alkaloid dimer or a pharmaceutically acceptable salt thereof for the preparation of an anti-inflammatory agent.
The technical scheme of the invention is summarized as follows:
alkaloid dimer, as shown in formula I or formula II:
the application of the alkaloid dimer or the pharmaceutically acceptable salt thereof in preparing anti-inflammatory drugs.
The invention has the advantages that:
the alkaloid dimer is separated from the conventional traditional Chinese medicine rhizoma corydalis Corydalis yanhusuo W.T.Wang. Experiments prove that the alkaloid dimer can obviously inhibit the function of LPS for inducing mouse macrophage RAW264.7 to release NO under the concentration of 5.0-20.0 mu M, wherein the IC of the alkaloid dimer II 50 The value is obviously stronger than that of the indometacin which is a clinically commonly used non-steroidal anti-inflammatory drug; IC of alkaloid dimer I 50 The value is equivalent to the effect of indomethacin. The above results suggest that the alkaloid dimers of the present invention can be used as anti-inflammatory drugs for further development.
Detailed Description
The present invention will be described in further detail with reference to examples, but embodiments of the present invention are not limited thereto.
The preparation of alkaloid dimer comprises the following steps:
50kg of tuber of rhizoma corydalis Corydalis yanhusuo W.T.Wang is added with 10L of 6% acetic acid aqueous solution by volume concentration for soaking for 24 hours, taken out and dried at 40 ℃; pulverizing, soaking in water for 30min, ultrasonic extracting for 1 hr, filtering, soaking the residue for 30min, ultrasonic extracting for 3 times, each time with 50L water, mixing the extractive solutions, and concentrating under reduced pressure to obtain extract; subjecting the extract to macroporous adsorbent resin (HPD-100) column chromatography, sequentially eluting with 20L water, 150L 50% ethanol water solution and 80L 95% ethanol water solution, sequentially collecting eluate, concentrating under reduced pressure to obtain eluate I, II and III, subjecting eluate III (250 g) to silica gel column chromatography, sequentially eluting with 5L dichloromethane-methanol mixed solution with volume ratio of 200:1, 180:1, 160:1, 140:1, 120:1, 100:1, 50:1, 10:1, sequentially collecting eluate, concentrating under reduced pressure, and drying to obtain component A, B, C, D, E, F, G, H;
component H (6.9 g) was eluted with a mixed solvent of petroleum ether, methylene chloride and methanol at a volume ratio of 5:5:1 by 600mL column chromatography on Sephadex LH-20, and the eluate was collected as one fraction per 200mL, concentrated under reduced pressure and dried to give components H-1, H-2 and H-3.H-3 (2.2 g) was purified by reverse phase ODS medium pressure column chromatography, eluting with 2L of 30% by volume aqueous methanol, concentrating the eluate under reduced pressure, and drying to give component H-3-1. The component H-3-1 (260 mg) is subjected to Sephadex LH-20 column chromatography, and is eluted by using 300mL of a mixed solvent consisting of petroleum ether, methylene dichloride and methanol with the volume ratio of 5:5:1, and each 100mL of eluent is collected as a fraction, and the fractions H-3-1-1, H-3-1-2 and H-3-1-3 are obtained sequentially after decompression concentration and drying. Subjecting H-3-1-3 to preparative liquid chromatography, eluting with 35% acetonitrile aqueous solution by volume, collecting t R Concentrating and drying under reduced pressure to obtain alkaloid dimer (5.0 mg, formula I) of formula I, collecting t R The fraction of 24.5min was concentrated under reduced pressure and dried to give the alkaloid dimer of formula II (3.0 mg, abbreviated as formula II).
Red amorphous powder; UV (MeOH) lambda max (logε)203.4(3.81),254.2(3.63),320.4(3.37),336.8(3.35),420.2(2.83),500.2(2.47)nm；IR(KBr)ν max 3405,3244,2931,1675,1469,1203,1141,845,803,724cm -1 ； 1 H NMR(DMSO-d 6 ,600MHz)and 13 C NMR(DMSO-d 6 150 MHz) data, see table 1; HRESIMS m/z 342.1230[ M] 2+ (calcd for C 41 H 36 N 2 O 8 ,342.1230).
Red amorphous powder; UV (MeOH) lambda max (logε)203.8(3.28),251.6(3.03),317.8(2.70),334.2(2.69),423.6(2.28),500.6(2.14)nm；IR(KBr)ν max 3440,3225,3078,2923,2856,1673,1470,1206,1137,843,803,726cm -1 ； 1 H NMR(MeOH-d 4 ,600MHz)and 13 C NMR(MeOH-d 4 150 MHz) data, see table 1; HRESIMS m/z 343.1309[ M ]] 2+ (calcd for C 41 H 38 N 2 O 8 ,343.1309).
TABLE 1 biological basic I, formula II 1 H-NMR 13 C-NMR (600 MHz) data
The structures of formula I and formula II were identified by physicochemical constants and modern spectroscopy means (UV, IR, HRMS, NMR), formula I being named as extended Hu Suoshuang base A (Yanhusuosine A) and formula II being named as extended Hu Suoshuang base B (Yanhusuosine B) as follows:
example 2
Pharmacological experiments
(1) Assay for inhibiting LPS-induced Nitric Oxide (NO) release by mouse macrophage RAW264.7 by alkaloid dimers shown in formula I and formula II
Instrument: enzyme label instrument
Reagent: griess method NO detection kit (Biyun Tian)
The experimental steps are as follows:
the isolated alkaloid dimers of formula I and formula II were examined for their ability to inhibit LPS-induced release of NO by mouse macrophage RAW264.7 (commercial product) by the Griess method.
Taking the plant with good growth state and logarithmic phase, and the concentration is 1×10 6 100 mu L of cell/mL was inoculated into a 96-well plate at 37℃with 5% CO 2 Culturing in an incubator for 24 hours. After 24h, 100. Mu.L of DMEM cell culture medium containing LPS (final concentration 0.5. Mu.g/mL) and different drugs (final concentration 100. Mu.M, 50. Mu.M, 10. Mu.M, 5. Mu.M, 1. Mu.M) was added to each well, and the blank and LPS groups were set up at 37℃with 5% CO 2 Culturing for 36h. After 36h, the culture supernatant was taken, the NO content in the culture supernatant was measured and calculated according to the standard procedure of the NO detection kit instructions.
The obtained alkaloid dimers of formula I and formula II were tested for their activity in inhibiting LPS-induced Nitric Oxide (NO) production by mouse macrophages according to the procedure described above, and the results are shown in Table 2.
TABLE 2 alkaloid dimers of formulas I and II inhibit LPS-induced nitric oxide release activity of mouse macrophage RAW264.7
The alkaloid dimer and the pharmaceutically acceptable salt thereof are prepared into preparations in application forms suitable for oral administration or injection and the like by the conventional technical means, and pharmaceutically acceptable carriers and/or excipients, such as: tablets, capsules, powders, syrups or injections, etc. The preparation has the function of inhibiting excessive NO production by organisms.
The above description of the embodiments is only intended to assist in understanding the method of the invention and its central ideas. It should be noted that it will be apparent to those skilled in the art that various changes and modifications can be made herein without departing from the principles of the invention, which also falls within the scope of the appended claims.
Claims (2)
1. An alkaloid dimer is characterized by being shown in a formula (I) or a formula (II):
2. use of the alkaloid dimer according to claim 1, or a pharmaceutically acceptable salt thereof, for the preparation of an anti-inflammatory agent.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110372731A (en) * | 2019-08-14 | 2019-10-25 | 昆明理工大学 | Quinoline-yaruru alkaline bisindole alkaloid compound and its application |
| CN110372732A (en) * | 2019-08-14 | 2019-10-25 | 昆明理工大学 | Aspidospermine-quinoline type dimeric indole alkaloid compound and its application |
| CN113980034A (en) * | 2021-09-08 | 2022-01-28 | 中国医学科学院药用植物研究所 | Dendrobium roseum indole alkaloid compound, preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110372731A (en) * | 2019-08-14 | 2019-10-25 | 昆明理工大学 | Quinoline-yaruru alkaline bisindole alkaloid compound and its application |
| CN110372732A (en) * | 2019-08-14 | 2019-10-25 | 昆明理工大学 | Aspidospermine-quinoline type dimeric indole alkaloid compound and its application |
| CN113980034A (en) * | 2021-09-08 | 2022-01-28 | 中国医学科学院药用植物研究所 | Dendrobium roseum indole alkaloid compound, preparation method and application |
Non-Patent Citations (1)
| Title |
|---|
| (+)/(−)-Yanhusuosines A and B, two dimeric benzylisoquinoline-protoberberine alkaloid atropo-enantiomers featuring polycyclic skeletons from Corydalis yanhusuo;Guiyang Xia，等;《Chinese Chemical Letters》;第34卷;108073 * |
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