CN115636807A - Preparation method and application of two 2-aryl benzofuran derivatives - Google Patents
Preparation method and application of two 2-aryl benzofuran derivatives Download PDFInfo
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Abstract
The invention discloses a preparation method of two 2-aryl benzofuran derivatives and application thereof in preparing medicaments for treating inflammatory diseases. The 2-aryl benzofuran derivatives are two new compounds named as Polomargillin B and Polomargillin C, and have the following structures:
the compounds have strong effects on rat neutrophil respiratory burstPotent inhibitory activity, IC thereof 50 Respectively 0.27 +/-0.10 mu M and 1.53 +/-0.58; the two compounds can be further prepared into medicines for treating inflammatory diseases, and are used for clinically treating various oxidative damages caused by excessive activation of neutrophils, such as rheumatoid arthritis, compensatory anti-inflammatory response syndrome, systemic inflammatory response syndrome and the like.
Description
Technical Field
The invention belongs to the field of medicines, relates to a preparation method of two 2-aryl benzofuran derivatives, and particularly relates to application of two 2-aryl benzofuran derivatives, namely, peroxomonosulfatin B and peroxomonosulfatin C extracted and separated from peroxomonosulfan in preparation of medicines for treating inflammatory diseases.
Background
Neutrophils (PMNs) are the first line of defense of the human body against the invasion of foreign pathogens; when PMNs recognize small peptides secreted by receptors or complexes formed by bacteria and antibodies in serum, the PMNs are mediated by receptors on membranes to cause activation of cells, and a large amount of superoxide anions (O) are rapidly generated 2 ·- )；O 2 ·- Under the catalysis of superoxide dismutase and myeloperoxidase, a series of free radical chain reactions occur to generate various Reactive Oxygen Species (ROS) including hydroxyl radical (HO.), and hydrogen peroxide (H) 2 O 2 ) And hypochlorous acid (HOCl); these ROS can efficiently destroy invading pathogenic microorganisms, a phenomenon known as respiratory outbreak; under normal physiological conditions, the respiratory burst of PMNs is accurately regulated and controlled, and the most effective pathogenic bacteria resisting mechanism of the body is formed; however, ROS can also damage surrounding normal tissues while killing invading bacteria, causing blockage of microcirculation, damage to vascular endothelial cells and extravascular tissue cells, and release and promotion of release of inflammatory mediators, which become "victims"; in patients with rheumatoid arthritis, for example, neutrophils are improperly activated, and a large amount of ROS is produced to cause the erosion of articular cartilage tissues; also, for example, in sepsis or surgical injury, trauma, burns, ischemia reperfusion injury, over-activated PMNs can cause tissue damage and, in severe cases, result in uncontrolled inflammatory responses, including compensatory anti-inflammatory response syndrome (cARS), systemic Inflammatory Response Syndrome (SIRS), and the like; therefore, the discovery of substances that inhibit the respiratory burst of PMNs is of great importance in the treatment of various oxidative insults caused by the respiratory burst of PMNs.
The separation and identification of natural products with novel structures and remarkable activities from natural medicines is one of the main ways for finding new medicines; artocarpus heterophyllus (Artocarpus styracifolius Pierre) is a tree species of Artocarpus of Moraceae; the Polo honey is sweet, slightly sour, mild and nontoxic and has the effects of quenching thirst, relieving restlessness, sobering up and tonifying qi; modern chemical and pharmacological studies show that the purrocarpus is rich in a large amount of isopentenyl phenolic components which have wide pharmacological activity; in the activity screening in the early stage of research, the chloroform extraction part of the 95% ethanol extract of the Artocarpus heterophyllus root shows stronger inhibitory activity on the respiratory burst of rat PMNs. Therefore, the present inventors have conducted intensive studies on the active site.
Disclosure of Invention
In view of the above problems, the present invention provides two 2-arylbenzofuran derivatives (polomannin B and polomannin C) and their preparation method and application.
The technical scheme of the invention is as follows:
the two 2-aryl benzofuran derivatives have substances for inhibiting PMNs respiratory burst activity, and provide medicaments for clinically treating inflammation related to PMNs respiratory burst; the invention particularly relates to two 2-aryl benzofuran derivatives extracted from Artocarpus heterophyllus roots, namely Artocarpus B and Artocarpus C; the chemical structural formula of the compound is as follows:
further, the compounds 1 and 2 are two 2-arylbenzofuran derivatives, which are novel compounds not reported in the literature, namely, the poloxamine B and the poloxamine C.
Further, a preparation method of the two 2-aryl benzofuran derivatives, namely the poloxamine B and the poloxamine C;
specifically, the compound of the invention is prepared by the following method:
taking 17.0kg of Artocarpus heterophyllus root, leaching with 95% ethanol at room temperature for 3 times (medicinal material and solvent 1;
suspending the total extract with water 1:1, sequentially extracting with petroleum ether, chloroform, ethyl acetate, and n-butanol to obtain 213.3g of petroleum ether fraction, 574.0g of chloroform fraction, 382.0g of ethyl acetate fraction, and 152.4g of n-butanol fraction;
extracting chloroform extract 532.0g, mixing with HP-20 macroporous adsorbent resin (1:1), loading onto HP-20 type macroporous adsorbent resin column (column specification: 10 × 45cm), and gradient eluting with ethanol-water (0-95%) to obtain 11 fractions Frs.H1-H11;
fraction Fr.H6 (57.3 g) was subjected to ODS column chromatography (column size: 4X 22cm), meOH-H 2 O (volume ratio 4;
fraction Fr.H6O3 (13.7 g) was subjected to MCI CHP-20P resin column chromatography (column specification: 4X 45cm), meOH-H 2 O (volume ratio 6;
fraction fr.h6o3mm 4 (1.6 g)) was further subjected to Sephadex LH-20 gel column chromatography (column specification: 2 × 200cm)), methanol elution to obtain 7 fractions frs.h6o3m4l1-H6O3M4L7;
fraction H6O3M4L4 (82.0 mg)) was subjected to preparative high performance liquid column chromatography (column specification: 2 × 25cm), 50% acetonitrile elution, obtaining the compound poromitin B (1) of the invention;
fraction fr.h6o3m4l6 (74.0 mg) was subjected to preparative high performance liquid chromatography (column specification: 2 × 25cm), 50% acetonitrile elution, to obtain the compound of the invention, poromitin C (2).
Further, the invention aims to provide a new application of the compounds (two 2-aryl benzofuran derivatives, namely poloxamine B and poloxamine C and physiologically acceptable salts thereof) in preparing medicaments for treating inflammatory diseases (inflammation caused by uncontrolled respiratory burst of PMNs).
Furthermore, the inflammatory disease refers to diseases related to or similar to rheumatoid arthritis, compensatory anti-inflammatory response syndrome, systemic inflammatory response syndrome and the like.
The invention has the beneficial effects that: the activity screening experiment proves that the poloxamine B and the poloxamine C have obvious inhibition effect on the neutrophil explosion of rats stimulated by the fosaprepitant (PMA) and half Inhibition Concentration (IC) 50 ) Are each 0.27 +/-0.10 and 1.53 +/-0.58 mu M, and the activity is superior to that of a positive control V c (IC 50 =23.84 ± 2.20 μ M); the polomannin B and the polomannin C can be further prepared into medicines for treating inflammation caused by uncontrolled respiratory burst of PMNs.
Drawings
FIG. 1 is the chemical structural formula of Polomargin B (1) and Polomargin C (2) in the present invention;
FIG. 2 is a high resolution mass spectrum of the novel compound of the present invention, peromitin B (1);
FIG. 3 shows the NMR spectrum of a novel compound of Peromitin B (1) of the present invention: ( 1 H NMR) pattern;
FIG. 4 shows Polo, a novel compound of the present invention nuclear magnetic resonance carbon spectrum of meletin B (1) ((C)) 13 C NMR) chart;
FIG. 5 is the nuclear magnetic resonance DEPT 135 spectrum of the new compound of Peromitin B (1) in the invention
FIG. 6 is the nuclear magnetic resonance HSQC spectrum of the new compound of Peromitin B (1) in the invention
FIG. 7 is a nuclear magnetic resonance HMBC spectrum of a new compound of the invention, namely, peromannin B (1);
FIG. 8 is a high resolution mass spectrum of the novel compound of the present invention, peromitin C (2);
FIG. 9 shows the NMR spectra of the novel compound Peromelanin C (2) of the present invention: ( 1 H NMR) pattern;
FIG. 10 shows the NMR spectrum of a novel compound of Peromitin C (2) of the present invention: ( 13 C NMR) pattern;
FIG. 11 is a nuclear magnetic resonance DEPT 135 spectrum of the new compound of Peromitin C (2) in the present invention;
FIG. 12 is a nuclear magnetic resonance HSQC spectrum of the novel compound of the present invention, peromitin C (2);
FIG. 13 is a nuclear magnetic resonance HMBC spectrum of the new compound of the present invention, perlumin C (2);
FIG. 14 is a schematic diagram showing the correlation between the major HMBC (H → C) of the novel compounds of the present invention, perlumidin B (1) and Perlumidin C (2).
Detailed Description
In order to more clearly illustrate the technical solution of the present invention, the following detailed description is made with reference to the accompanying drawings:
example 1
Preparation of Polo Honey Bo Luo Misu B and Polo Honey C:
taking 17.0kg of Artocarpus heterophyllus root, leaching with 95% ethanol at room temperature for 3 times (medicinal material and solvent 1;
suspending the total extract with water 1:1, sequentially extracting with petroleum ether, chloroform, ethyl acetate, and n-butanol to obtain 213.3g of petroleum ether fraction, 574.0g of chloroform fraction, 382.0g of ethyl acetate fraction, and 152.4g of n-butanol fraction;
extracting chloroform extract 532.0g, mixing with HP-20 macroporous adsorbent resin (1:1), loading onto HP-20 type macroporous adsorbent resin column (column specification: 10 × 45cm), and gradient eluting with ethanol-water (0-95%) to obtain 11 fractions Frs.H1-H11;
fraction Fr.H6 (57.3 g) was subjected to ODS column chromatography (column size: 4X 22cm), meOH-H 2 O (volume ratio 4;
fraction Fr.H6O3 (13.7 g) was subjected to MCI CHP-20P resin column chromatography (column specification: 4X 45cm), meOH-H 2 O (volume ratio 6;
the fraction Frs.H6O3M4 (1.6 g) is further subjected to Sephadex LH-20 gel column chromatography (column specification: 2 x 200cm), and methanol elution is carried out to obtain 7 fractions Frs.H6O3M4L1-H6O3M4L7;
the fraction H6O3M4L4 (82.0 mg) was subjected to preparative high performance liquid chromatography (column specification: 2X 25cm) and eluted with 50% acetonitrile to give the compound Peromitin B of the present invention (4.0 mg, t. Mu.l; 0mg, g; t. Mu.l; n.g; n.b.) R 45min)；
Fraction Fr.H6O3M4L6 (74.0 mg) was subjected to preparative high performance liquid chromatography (column specification: 2 × 25cm) and eluted with 50% acetonitrile to give Peromannin C (15.6mg, t. Sup. T. Of the compound of the present invention R 35min)。
Example 2
Structural identification of Borreria Luo Misu B and Borreria C in Polo honey:
the isolated monomers were identified as two 2-arylbenzofuran compounds by high resolution mass spectrometry (HR-ESI-MS) and nuclear magnetic resonance spectroscopy (1D NMR and 2D NMR). Both compounds 1 and 2 are novel compounds not reported in the literature.
Infrared spectrum IR shows that a hydroxyl group (3357 cm) exists in the structure -1 ) Methyl (2925 cm) -1 ) And benzene rings (1616, 1481 cm) -1 ) Equal characteristic signal peaks;
1 the H NMR spectrum (Table 1) shows the signals delta for three active hydrogen protons H 9.43 (2H, s), 8.44 (1H, s)); a is 2 B spin coupling system signal delta H 6.71 (2h, d, j = 2.2hz), 6.23 (1h, t, j = 2.2hz); a methoxy signal delta H 3.94 (3H, s); in combination with the 13C NMR spectra, the proton and carbon signals delta for two typical groups of 3-methyl-2-butene substituents can be observed H 5.27 (1H, br t, J = 7.2Hz), 3.51 (2H, d, J = 7.2Hz), 1.83 (3H, s), 1.64 (3H, s), 5.13 (1H, br t, J = 6.9Hz), 3.33 (2H, d, J = 6.9Hz), 1.73 (3H, s) and 1.62 (3H, s); delta c 130.7、129.6、124.0、122.6、25.6、22.9、22.7、17.9、17.8；
Process for preparation of Compound 1 1 H NMR data and known Pregafur A derivatives of isopentenyl-2-arylbenzofuran [15] Very similar; the difference between the hydrogen spectra is mainly reflected in that the compound 1 lacks the proton signal delta which is assigned as H-2 in the regiafruan A H 6.85, and a group of proton signals which are assigned to 3-methyl-2-butene substituent groups are added; these data suggest that 1 is a 2-isopentenyl-substituted derivative of regioafuran a;
by DEPT 135, HSQC and HMBC NMR experiments, the position of the substituent was determined and all hydrogen and carbon signals were assigned (Table 1);
the substitution of the two isopentenyl groups at C-2 and C-4, respectively, can be determined by the observed HMBC correlation (FIG. 2) as follows: h 2 -15(δ H 3.51 Is with C-1 (. Delta.) C 152.9)、C-2(δ C 106.8 And C-3 (. Delta.) C 150.4 Correlation); h-16 (delta) H 5.27 Is related to C-2; h-20 (delta) H 3.33 With C-3, C-4 (. Delta.) C 116.1 And C-5 (. Delta.) C 148.5 ) are correlated; h-21 (delta) H 5.13 Is related to C-4;
in addition, the methoxy proton signal δ H 3.94 (MeO-5) correlation with HMBC at C-5 (Δ C148.5) confirms its substitution at C-5;
a comprehensive analysis of the HMBC correlation peak data confirmed that the structure of 1 was 5- [ 6-hydroxy-4-methoxy-5,7-bis (3-methyl-2-butene) benzofuran-2-yl ] -1,3-benzenediol (FIG. 1), which was named Polomannin B.
TABLE 1 of Compounds 1 and 2 1 H NMR and 13 c NMR spectrum data
a Bruker Avance 600 nmr; chemical shift reference solvent peak correction of deuterated dimethyl sulfoxide (delta) H 2.50；δ C 39.5)
b Bruker Avance 600 nmr; chemical shift correction (delta) with reference to solvent peak of deuterated methanol H 3.31；δ C 49.0)
Process for preparation of Compound 2 1 H and 13 c spectra and known isopentenyl 2-arylbenzofuran derivatives artemindonesianin A-1 [16] Very similar;
the main difference between the two is2 by a typical set of 2,2-dimethylchromene groups fused to a benzene ring (isopentenyl in cyclized form) H 6.63(1H,d,J＝10.0Hz)、5.52(1H,d,J＝10.0Hz)、1.45(3H×2,s)；δ C 118.0、127.6、77.9、28.2；
Meanwhile, 2 the NMR data of known compound artoindenoesinin A-1 was deleted and the signal δ was ascribed to 4-OMe H 3.93 and δ C 56.0; these information suggest that 2 is a 2-arylbenzofuran derivative containing two 2,2-dimethylchromene groups; by analyzing DEPT 135, HSQC and HMBC NMR spectra of 2, the fused position of two 2,2-dimethylchromene groups on the benzene ring was determined and all hydrogen and carbon signals were assigned (Table 1);
the fusion of the two 2,2-dimethylchromene groups at the C-2/C-3 and C-4/C-5 positions, respectively, can be confirmed by the following HMBC related signals: h-15 (delta) H 6.73 Is with C-1 (. Delta.) C 152.8)、C-2(δ C 100.9 And C-3 (. Delta.) C 148.0 Correlation); h-16 (delta) H 5.61 Is related to C-1;
H-20(δ H 6.63 With C-3, C-4 (. Delta.) C 106.7)、C-5(δ C 147.4 Correlation and H-21 (delta) H 5.52 Is related to C-4; a comprehensive analysis of the HMBC data confirmed that the structure of 2 was 5- [2H,9H-2,2,9,9-tetramethyl-furo [2,3-f]Pyrano [2,3-h][1]Benzopyran-6-yl]1,3-benzenediol (fig. 1), named Polomargin C.
Example 3
Cytotoxicity evaluation experiments with polo honey B and polo honey C:
rat PMNs are separated and purified by adopting the following experimental steps; taking a clean-grade SD rat (Experimental animal center of Jiangxi traditional Chinese medicine university, animal qualification number: JZDW 2011304), taking 9mL of blood from an orbit, and vertically dropping the blood into a glass centrifuge tube which is anticoagulated by 1mL of 1% heparin sodium; adding 4.5% dextran T-500 normal saline solution according to the proportion of 5:1, mixing uniformly, standing for about 1 hour at 4 ℃; taking supernatant, adding the supernatant into a centrifugal tube which is pre-filled with lymphocyte separation liquid according to the proportion of 3:1, centrifuging for 15 minutes at 800 r/min (275 g), taking out the centrifugal tube, dividing the centrifugal tube into three layers, wherein the upper layer is faint yellow serum, the middle white fog region is mononuclear cells and lymphocytes, and the lower layer is PMNs when settled to the bottom of the tube; discarding the supernatant, adding 2mL of special separation solution, rinsing once, shaking, and centrifuging at 2500 rpm (531 g) for 5 minutes; discarding the supernatant, adding 2mL of double distilled water into each centrifugal tube, blowing, shaking for 20 seconds (swelling red blood cells), immediately adding 2mL of 1.8% NaCl solution, mixing uniformly, centrifuging at 2500 rpm (531 g) for 5 minutes, discarding the supernatant, and repeating the operation until no blood cells remain; rinsing with HBSS-FCS buffer solution for 1-2 times (2 mL each time), centrifuging at 2500 rpm (531 g) for 3 min, and discarding supernatant; separating to obtain PMNs, adding 2mL HBSS-FCS buffer solution again, mixing evenly, measuring the activity by trypan blue staining method (the activity of PMNs is more than 95% in 3 h), and storing at 4 ℃ as cell mother suspension for standby.
Determining the cytotoxicity of Polo Honey B and Polo Honey C against PMNs with reference to literature relating to the standard trypan blue exclusion method; taking 50 μ L PMNs cell mother suspension, diluting with HBSS solution of 2% calf serum to cell concentration of 2 × 10 6 Per mL; 1mL of PMNs cell dilution was mixed with 10. Mu.L DMSO or test compound (dissolved in DMSO to a final concentration ranging from 1 to 1000. Mu.M) and incubated at 37 ℃ for 30 min; adding 112 μ L of 0.4% trypan blue dye solution into each sample, and calculating the cytotoxicity effect of the samples on PMNs by counting the condition that 100 cells absorb trypan blue under a high-power microscope; the results show that polo honey B and polo honey C are not significantly cytotoxic to PMNs at concentrations below 150. Mu.M.
Example 4
Determination of inhibition rate of PMNs respiratory outbreaks in rats by Polo Honey B and Polo Honey C:
rat PMNs cell mother suspensions were prepared using the same procedure as in example 3; taking 50 μ L PMNs cell mother suspension, diluting with HBSS solution of 2% calf serum to cell concentration of 2 × 10 6 Per mL; storing at 4 deg.C; PMNs are activated by an exogenous stimulant, namely phorbol myristate ethyl (PMA), to generate respiratory burst and a large amount of active oxygen radicals, the free radicals are captured by luminol serving as a luminescent agent to generate Chemiluminescence (CL), and the PMN-CL strength is positively correlated with the number of cells of the PMNs and the respiratory burst and phagocytic function of the PMNs; BPCL-K ultra-weak light-emitting measuring instrument (Beijing biophysical research of Chinese academy of sciences)Institute, the supporting BPCL appl.7.2 data processing workstation) parameters were set as: the temperature of the luminous pool is 37 ℃, the voltage value is 800V, the longest detection time is 1800s, and the counting time interval is 5s;
preheating the instrument for half an hour before use, and taking a base line; after the baseline is stable, 1ml of PMNs cell diluent is put into a luminescent cup, 200 mul of luminol working solution is added into the luminescent cup, the luminescent cup is placed into an ultra-weak luminescence measuring instrument to be incubated for 10min (the parameter setting is that the temperature of a luminescent pool is 37 ℃, the voltage is 800V, the longest detection time is 1800 s), and the self-luminescence process is recorded (the counting time interval is 5 s); then 10. Mu.l of sample solution (10. Mu.l DMSO as solvent control) was added and the assay was continued for 5min, 8. Mu.g.ml was added -1 Continuously measuring 10 μ l PMA stimulant for 15min, and recording the measurement result; PMN-CL intensity is expressed as luminescence count peak height; the PMN-CL inhibition rate is calculated according to the formula (1):
the PMN-CL inhibition rate is used as the ordinate, the sample concentration is used as the abscissa, a dose-effect relation curve is established, and the concentration of the sample (namely IC) when the luminescence inhibition rate is 50 percent can be calculated through the dose-effect curve 50 A value); with vitamin C (V) c ) As a positive control;
the results show that the two stilbene compounds have obvious inhibition effect on PMN outbreak of rats stimulated by PMA, and the IC of the stilbene compounds 50 0.27 +/-0.10 and 1.53 +/-0.58 mu M respectively, which are superior to the positive control V c (IC 50 ＝23.84±2.20μM)。
Finally, it should be understood that the embodiments described herein are merely illustrative of the principles of embodiments of the present invention; other variations are also possible within the scope of the invention; thus, by way of example, and not limitation, alternative configurations of embodiments of the invention may be considered consistent with the teachings of the present invention; accordingly, the embodiments of the invention are not limited to the embodiments explicitly described and depicted.
Claims (5)
1. Two 2-arylbenzofuran derivatives, comprising poloxamine B and poloxamine C; the chemical structural formula of the compound is as follows:
2. a process for the preparation of two 2-arylbenzofuran derivatives as claimed in claim 1.
3. Use of two 2-arylbenzofuran derivatives and their physiologically acceptable salts, prepared by the process according to claim 2, for the preparation of a medicament for the treatment of inflammatory diseases.
4. The use according to claim 3, wherein the inflammatory disease is an inflammatory disease caused by uncontrolled respiratory bursts of PMNs.
5. The use according to claim 3, wherein said inflammatory disease is rheumatoid arthritis, compensatory anti-inflammatory response syndrome or systemic inflammatory response syndrome.
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| CN101829079A (en) * | 2009-03-13 | 2010-09-15 | 复旦大学 | Application of compound of (E)-5-[6-hydroxy-5-(3-methyl-1-butenyl)-2-benzofuranyl] phenyl-1, 3-diol to preparation of pancrelipase inhibitor |
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