CN115636807B - Preparation method and application of two 2-arylbenzofuran derivatives - Google Patents
Preparation method and application of two 2-arylbenzofuran derivatives Download PDFInfo
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Abstract
The invention discloses a preparation method of two 2-arylbenzofuran derivatives and application thereof in preparing medicines for treating inflammatory diseases. The 2-arylbenzofuran derivatives are two novel compounds named as corollary honey B and corollary honey C from the genus corollary honey Artocarpus heterophyllus lam of the family Moraceae, and have the following structures:the compound has strong inhibitory activity on respiratory burst of neutrophils in rats, and IC thereof 50 0.27.+ -. 0.10. Mu.M and 1.53.+ -. 0.58, respectively; the two compounds can be further used for preparing medicines for treating inflammatory diseases, and can be used for clinically treating various oxidative damages caused by neutrophil overactivation, such as rheumatoid arthritis, compensatory anti-inflammatory reaction syndrome, systemic inflammatory reaction syndrome and the like.
Description
Technical Field
The invention belongs to the field of medicines, relates to a preparation method of two 2-arylbenzofuran derivatives, and particularly relates to application of two 2-arylbenzofuran derivatives, namely, corollenin B and corollenin C, extracted and separated from corollenin in preparation of medicines for treating inflammatory diseases.
Background
Neutrophils (PMNs) are the first line of defense of the human body against invasion of foreign pathogens; when PMNs recognize small peptides secreted by the receptor or complexes formed by bacteria and antibodies in serum, cell activation is mediated by the receptor on the membrane, rapidly generating large amounts of superoxide anions (O 2 ·- )；O 2 ·- A series of free radical chain reactions are generated under the catalysis of superoxide dismutase and myeloperoxidase, and various Reactive Oxygen Species (ROS) are generated, including hydroxyl radicals (HO.) and hydrogen peroxide (H) 2 O 2 ) Hypochlorous acid (HOCl); these areROS can efficiently destroy invading pathogenic microorganisms, a phenomenon known as respiratory burst; under normal physiological conditions, the respiratory burst of PMNs is accurately regulated, and the most effective pathogenic bacteria resisting mechanism of the organism is formed; however, ROS can also cause damage to surrounding normal tissues while killing invasive bacteria, causing obstruction of microcirculation, damage of vascular endothelial cells and extravascular tissue cells, release and promotion of release of inflammatory mediators, becoming "destroys"; in rheumatoid arthritis patients, neutrophils are improperly activated, and the large amount of ROS generated causes erosion of articular cartilage tissue; in other cases, such as sepsis or surgical injury, trauma, burns, ischemia reperfusion injury, overactivated PMNs can cause tissue damage, in severe cases leading to uncontrolled inflammatory responses, including compensatory anti-inflammatory response syndrome (caras), systemic Inflammatory Response Syndrome (SIRS), etc.; thus, substances that inhibit PMNs respiratory bursts were found to be of great significance for the treatment of various oxidative damages caused by PMNs respiratory bursts.
The separation and identification of natural products with novel structures and remarkable activity from natural medicines is always one of the main ways of discovering new medicines; the Porro honey (Artocarpus styracifolius Pierre) is a tree species of Porro honey of Moraceae; the ' Ben Cao gang mu ' carrier, the ' sweet and slightly sour, flat and nontoxic ' of the Porrow ' honey has the effects of quenching thirst, relieving restlessness, sobering up and tonifying qi; modern chemistry and pharmacological research show that the pornogen is rich in a large amount of isopentenyl phenolic components, and the components have wide pharmacological activity; in the early-stage activity screening of the study, the chloroform extraction part of the 95% ethanol extract of the Porro honey root shows stronger inhibition activity on the respiratory burst of the rat PMNs. Accordingly, the present invention has been made in an intensive study of the active site.
Disclosure of Invention
In view of the above problems, it is an object of the present invention to provide a method for preparing two 2-arylbenzofuran derivatives (corollenin B and corollenin C) and applications thereof.
The technical scheme of the invention is as follows:
the two 2-arylbenzofuran derivatives have substances for inhibiting the respiratory burst activity of PMNs, and provide medicines for treating inflammation related to the respiratory burst of PMNs clinically; the invention relates to two 2-aryl benzofuran derivatives extracted from a Porro honey root, namely Porro honey B and Porro honey C; the chemical structural formula of the compound is shown as follows:
furthermore, the compounds 1 and 2 are two 2-arylbenzofuran derivatives, which are novel compounds not reported in the literature, namely the corollary honey B and the corollary honey C.
Further, the preparation method of the two 2-aryl benzofuran derivatives, namely the corollary honey B and the corollary honey C;
specifically, the compound of the present invention is prepared by the following method:
extracting 17.0kg of Porro honey root with 95% ethanol at room temperature for 3 times (the ratio of the medicinal materials to the solvent is 1:10) to obtain extract, filtering, mixing, and concentrating under reduced pressure to obtain total extract 1.5kg;
suspending the total extract with water at a ratio of 1:1, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butanol to obtain petroleum ether 213.3g, chloroform 574.0g, ethyl acetate 382.0g and n-butanol 152.4g;
taking 532.0g of chloroform extract, mixing with HP-20 macroporous adsorption resin (weight ratio 1:1), loading onto HP-20 macroporous adsorption resin column (column specification: 10 x 45 cm), and gradient eluting with ethanol-water (0-95%) to obtain 11 fractions Frs.H1-H11;
the fraction Fr.H6 (57.3 g) was subjected to ODS column chromatography (column size: 4X 22 cm), meOH-H 2 O (volume ratio 4:6,5:5,6:4,7:3,8:2,9:1, 10:0) to obtain 6 fractions Frs.H6O1-H6O6;
the fraction Fr.H6O3 (13.7 g) was purified by MCI CHP-20P resin column chromatography (column size: 4X 45 cm), meOH-H 2 O (volume ratio 6:4,7:3,8:2,9:1, 10:0) to obtain 7 fractions Frs.H6O3M1-H6O3M7;
the fraction fr.h6o3m4 (1.6 g)) was further subjected to Sephadex LH-20 gel column chromatography (column specification: 2 x 200 cm)), methanol to obtain 7 fractions Frs.H6O3M4L1-H6O3M4L7;
fractions H6O3M4L4 (82.0 mg)) were subjected to preparative high performance liquid column chromatography (column specification: 2 x 25 cm), eluting with 50% acetonitrile to obtain the compound of the invention, namely, the corollary honey B (1);
fractions fr.h6o3m4l6 (74.0 mg)) were subjected to preparative high performance liquid column chromatography (column specification: 2 x 25 cm), 50% acetonitrile, to obtain the compound of the present invention, corollary honey C (2).
Further, the invention aims to provide a novel application of the compound (two 2-arylbenzofuran derivatives of the corollary honey B and the corollary honey C and physiologically acceptable salts thereof) in preparing medicines for treating inflammatory diseases (inflammation caused by uncontrolled breathing of PMNs).
Further, the inflammatory disease refers to rheumatoid arthritis, compensatory anti-inflammatory reaction syndrome and systemic inflammatory reaction syndrome and the like or similar diseases.
The beneficial effects of the invention are as follows: the activity screening experiments prove that the corollary honey B and the corollary honey C have obvious inhibition effect on the neutrophil burst of the rat stimulated by the ethyl Phorbol Myristate (PMA), and half Inhibition Concentration (IC) 50 ) The activities of the positive control V are better than that of positive control V at 0.27+/-0.10 and 1.53+/-0.58 mu M respectively c (IC 50 =23.84±2.20 μm); the corollary honey B and the corollary honey C can be further prepared into medicines for treating inflammation caused by uncontrolled breathing burst of PMNs.
Drawings
FIG. 1 shows chemical structural formulas of the corollary honey B (1) and the corollary honey C (2) in the invention;
FIG. 2 is a high resolution mass spectrum of novel compound, corollary honey B (1) in the invention;
FIG. 3 shows the nuclear magnetic resonance hydrogen spectrum of novel compound, namely, corollary honey B (1) 1 H NMR) map;
FIG. 4 shows nuclear magnetic resonance carbon spectrum of novel compound of Peromal sodium B (1) 13 C NMR) map;
FIG. 5 is a nuclear magnetic resonance DEPT 135 spectrum of novel compound, corollary honey B (1), in the present invention
FIG. 6 is a nuclear magnetic resonance HSQC spectrum of novel compound, corollary honey B (1) in the invention
FIG. 7 is a nuclear magnetic resonance HMBC spectrum of novel compound, corollary honey B (1) in the invention;
FIG. 8 is a high resolution mass spectrum of novel compound, corollary honey C (2) in the present invention;
FIG. 9 shows the hydrogen nuclear magnetic resonance spectrum of novel compound, corollary honey C (2) in the present invention 1 H NMR) map;
FIG. 10 shows nuclear magnetic resonance carbon spectrum of novel compound of corollary honey C (2) in the invention 13 C NMR) map;
FIG. 11 is a diagram showing the nuclear magnetic resonance DEPT 135 spectrum of novel compound, corollary honey C (2) in the present invention;
FIG. 12 is a nuclear magnetic resonance HSQC spectrum of novel compound, corollary honey C (2) in the invention;
FIG. 13 is a nuclear magnetic resonance HMBC spectrum of novel compound, corollary honey C (2) in the present invention;
fig. 14 is a schematic diagram showing the correlation of the main HMBC (h→c) of the novel compounds of the present invention, corollary honey B (1) and corollary honey C (2).
Detailed Description
In order to more clearly describe the technical scheme of the invention, the technical scheme of the invention is further described in detail below with reference to the accompanying drawings:
example 1
Preparation of the medium wave Luo Misu B and the corollary honey C:
extracting 17.0kg of Porro honey root with 95% ethanol at room temperature for 3 times (the ratio of the medicinal materials to the solvent is 1:10) to obtain extract, filtering, mixing, and concentrating under reduced pressure to obtain total extract 1.5kg;
suspending the total extract with water at a ratio of 1:1, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butanol to obtain petroleum ether 213.3g, chloroform 574.0g, ethyl acetate 382.0g and n-butanol 152.4g;
taking 532.0g of chloroform extract, mixing with HP-20 macroporous adsorption resin (weight ratio 1:1), loading onto HP-20 macroporous adsorption resin column (column specification: 10 x 45 cm), and gradient eluting with ethanol-water (0-95%) to obtain 11 fractions Frs.H1-H11;
the fraction Fr.H6 (57.3 g) was subjected to ODS column chromatography (column size: 4X 22 cm), meOH-H 2 O (volume ratio 4:6,5:5,6:4,7:3,8:2,9:1, 10:0) to obtain 6 fractions Frs.H6O1-H6O6;
the fraction Fr.H6O3 (13.7 g) was purified by MCI CHP-20P resin column chromatography (column size: 4X 45 cm), meOH-H 2 O (volume ratio 6:4,7:3,8:2,9:1, 10:0) to obtain 7 fractions Frs.H6O3M1-H6O3M7;
subjecting the fraction Fr.H6O3M4 (1.6 g) to Sephadex LH-20 gel column chromatography (column specification: 2 x 200 cm), eluting with methanol to obtain 7 fractions Frs.H6O3M4L1-H6O3M4L7;
the fraction H6O3M4L4 (82.0 mg) is subjected to preparative high performance liquid chromatography (column specification: 2 x 25 cm), and 50% acetonitrile is eluted, thereby obtaining the compound of the invention, namely, the coromnimin B (4.0 mg, t) R 45min)；
The fraction Fr.H6O3M4L6 (74.0 mg) is subjected to high performance liquid chromatography (column specification: 2 x 25 cm) and eluted with 50% acetonitrile to obtain the compound of the invention, namely, the corollary honey C (15.6 mg, t) R 35min)。
Example 2
Structural identification of the wave Luo Misu B and the corollary honey C in corollary honey:
the separated monomers were identified as two 2-arylbenzofurans 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.
Compound 1, pale yellow oil (methanol): high resolution Mass Spectrometry HR-ESI-MS gives an excimer ion peak m/z 407.1853[ M-H ]] - (C 25 H 27 O 5 Calculated as 407.1864)), and its molecular formula is determined as C 25 H 28 O 5 ；
IR spectrum IR showed that hydroxyl groups were present in the structure (3357 cm -1 ) Methyl (2925 cm) -1 ) And benzene ring (1616, 1481 cm) -1 ) An isocharacteristic signal peak;
1 the H NMR spectrum (Table 1) shows three active hydrogen proton signals delta H 9.43(2H,s)、8.44 (1H, s)); a is A 2 B spin-coupled system signal delta H 6.71 (2h, d, j=2.2 Hz), 6.23 (1 h, t, j=2.2 Hz); methoxy signal delta H 3.94 (3H, s); in combination with 13C NMR spectra, two typical proton and carbon signals delta of the 3-methyl-2-butene substituent groups can be observed H 5.27 (1 h, br t, j=7.2 Hz), 3.51 (2 h, d, j=7.2 Hz), 1.83 (3 h, s), 1.64 (3 h, s), 5.13 (1 h, br t, j=6.9 Hz), 3.33 (2 h, d, j=6.9 Hz), 1.73 (3 h, s) and 1.62 (3 h, s); delta c 130.7、129.6、124.0、122.6、25.6、22.9、22.7、17.9、17.8；
Compound 1 1 H NMR data and known isopentenyl 2-arylbenzofuran derivatives Regiafuran A [15] Very similar; the difference between the two hydrogen spectra is mainly shown by the deletion of the proton signal delta belonging to H-2 in Regiafuran A in the compound 1 H 6.85, but a set of proton signals ascribed to the 3-methyl-2-butene substituent; these data suggest that 1 is a 2-isopentenyl substituted derivative of regiafuran a;
the position of the substituents was determined and all hydrogen and carbon signals were attributed by DEPT 135, HSQC and HMBC NMR experiments (Table 1);
the substitution of the two isopentenyl groups at C-2 and C-4, respectively, can be determined by the following HMBC correlation (FIG. 2) observed: h 2 -15(δ H 3.51 And C-1 (delta) C 152.9)、C-2(δ C 106.8 And C-3 (delta) C 150.4 A) correlation; h-16 (delta) H 5.27 C-2); h-20 (delta) H 3.33 C-3, C-4 (delta) C 116.1 And C-5 (delta) C 148.5 A) correlation; h-21 (delta) H 5.13 C-4);
in addition, methoxy proton signal delta H 3.94 (MeO-5) and C-5 (. Delta.c 148.5) HMBC correlation confirm that its substitution is at C-5;
comprehensive analysis of the HMBC correlation peak data established that 1 had the structure 5- [ 6-hydroxy-4-methoxy-5, 7-bis (3-methyl-2-butene) benzofuran-2-yl ] -1, 3-benzenediol (fig. 1), designated as corollary milm B.
Table 1 compounds 1 and 2 1 H NMR 13 C NMR spectroscopic data
a Bruker Avance 600 Nuclear magnetic resonance apparatus; chemical shift reference deuterated dimethyl sulfoxide solvent peak correction (delta H 2.50；δ C 39.5)
b Bruker Avance 600 Nuclear magnetic resonance apparatus; solvent peak correction (delta) of chemical shift reference deuterated methanol H 3.31；δ C 49.0)
Compound 2, pale yellow oil (methanol); high resolution Mass Spectrometry HR-ESI-MS gives an excimer ion peak m/z 389.1402[ M-H ]] - (C 24 H 21 O 5 Calculated as 389.1394), and its molecular formula is determined as C 24 H 22 O 5 ；
Compound 2 1 H and 13 spectrum C and known isopentenyl 2-arylbenzofuran derivatives, artoindonosian A-1 [16] Very similar;
the main difference between the two is that the signal delta of a group of typical 2, 2-dimethylchromene groups (the cyclized form of isopentenyl) fused with benzene rings is 2 more 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；
At the same time, 2 is deleted of the NMR data of the known compound artoindonesinin A-1, which is ascribed to the 4-OMe signal delta H 3.93 and delta C 56.0; these messages suggest that 2 is a 2-arylbenzofuran derivative containing two 2, 2-dimethylchromene groups; by analyzing the 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 attributed (Table 1);
the two 2, 2-dimethylchromene groups fused 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 With (d) and (d)C-1(δ C 152.8)、C-2(δ C 100.9 C-3 (delta) C 148.0 A) correlation; h-16 (delta) H 5.61 C-1);
H-20(δ H 6.63 C-3, C-4 (delta) C 106.7)、C-5(δ C 147.4 Correlation and H-21 (delta) H 5.52 C-4); complete analysis of HMBC data determines that 2 has the structure 5- [2H,9H-2, 9-tetramethyl-furo [2,3-f]Pyrano [2,3-h][1]Benzopyran-6-yl]-1, 3-benzenediol (figure 1), named corollary honey C.
Example 3
Cytotoxicity evaluation experiments of corollary honey B and corollary honey C:
the following experimental steps were used to isolate and purify rat PMNs; taking clean SD rats (laboratory animal center of Jiangxi university, animal pass number: JZDW 2011304), taking 9mL of blood from the orbit, and vertically dripping into a glass centrifuge tube anticoagulated with 1mL of 1% heparin sodium; adding 4.5% dextran T-500 physiological saline solution at a ratio of 5:1, mixing, and standing at 4deg.C for about 1 hr; adding the supernatant into a centrifuge tube pre-filled with lymphocyte separation liquid according to the ratio of 3:1, centrifuging for 15 minutes at 800 revolutions per minute (275 g), taking out the centrifuge tube, and taking out three layers in the tube, wherein the upper layer is light yellow serum, the middle white mist area is mononuclear cells and lymphocytes, and the lower layer is PMNs which are settled at the bottom of the tube; the supernatant was discarded, and 2mL of the special separation solution was added for rinsing once, and after shaking, the mixture was centrifuged at 2500 rpm (531 g) for 5 minutes; removing the supernatant, adding 2mL of double distilled water into each centrifuge tube, blowing, shaking for 20 seconds (swelling red blood cells), immediately adding 2mL of 1.8% NaCl solution, mixing, centrifuging for 5 minutes at 2500 rpm (531 g), removing the supernatant, and repeating the operation until no blood cells remain; rinsing with HBSS-FCS buffer for 1-2 times, centrifuging at 2500 rpm (531 g) for 3 min each time with 2mL of HBSS-FCS solution, and discarding supernatant; separating to obtain PMNs, adding 2mL of HBSS-FCS buffer again, mixing, measuring activity by trypan blue staining method (activity of PMNs >95% in 3 h), and preserving at 4deg.C to obtain cell mother suspension for later use.
Cytotoxicity of both corollary honey B and corollary honey C on PMNs was determined with reference to the literature relevant to the standard trypan blue exclusion method; mu.L of PMNs cell stock suspension was taken, and 2% of the stock suspension was usedHBSS solution of bovine serum was diluted to a cell concentration of 2X 10 6 individual/mL; 1mL of PMNs cell dilutions were mixed with 10. Mu.L of DMSO or test compound (dissolved in DMSO at a final concentration ranging from 1 to 1000. Mu.M) and incubated for 30 min at 37 ℃; the cytotoxic effect of samples on PMNs was calculated by counting 100 cells absorbing trypan blue under a high power microscope with 112 μl of 0.4% trypan blue dye solution added to each sample; the results show that both corollary honey B and corollary honey C have no significant cytotoxicity to PMNs at concentrations below 150 μm.
Example 4
Determination of respiratory burst inhibition rate of PMNs in rats by corollary honey B and corollary honey C:
a rat PMNs cell mother suspension was prepared by the same procedure as in example 3; 50. Mu.L of PMNs cell stock suspension was diluted to a cell concentration of 2X 10 with HBSS solution of 2% calf serum 6 individual/mL; preserving at 4 ℃ for standby; PMNs undergo respiratory burst after being activated by an exogenous stimulator, phorbol ethyl ester (PMA), generating a large amount of active oxygen free radicals, which are captured by luminol, a luminol-emitting agent, to generate Chemiluminescence (CL), the PMN-CL intensity being positively correlated with the cell number of PMNs and the respiratory burst and phagocytic function of PMNs; the parameters of the BPCL-K ultra-weak luminescence measuring instrument (matched with the BPCL appl.7.2 data processing workstation of Beijing biophysical institute of academy of sciences of China) are set as follows: 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 baseline; after the baseline is stable, 1ml of PMNs cell diluent is taken out in a luminous cup, 200 mu l of luminol working solution is added into the PMNs cell diluent, the PMNs cell diluent is placed in an ultra-weak luminous measuring instrument for incubation for 10min (parameter setting: luminous pool temperature 37 ℃, voltage 800V and maximum detection time 1800 s), and a self-luminous process (counting time interval 5 s) is recorded; then 10. Mu.l of sample solution (using 10. Mu.l DMSO as solvent control) was added for further measurement for 5min, 8. Mu.g.ml was added -1 10 μl of PMA stimulator is measured continuously for 15min, and the measurement result is recorded; PMN-CL intensities are expressed in terms of luminescence count peak heights; the PMN-CL inhibition is calculated according to formula (1):
taking PMN-CL inhibition rate as ordinate and sample concentration as abscissa, establishing a dose-response relationship curve, and calculating the concentration of the sample (namely IC) at 50% luminescence inhibition rate by the dose-response curve 50 A value); with vitamin C (V) c ) As a positive control;
the results show that the two stilbene compounds have remarkable inhibition effect on PMA stimulated rat PMNs burst and IC thereof 50 0.27+ -0.10 and 1.53+ -0.58 μM, respectively, are superior to 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 the embodiments of the present invention; other variations are 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 in keeping with the teachings of the invention; accordingly, the embodiments of the present invention are not limited to the embodiments explicitly described and depicted herein.
Claims (4)
1. Two 2-arylbenzofuran derivatives, wherein the two 2-arylbenzofuran derivatives are corollary honey B and corollary honey C; the chemical structural formula of the compound is shown as follows:
2. use of two 2-arylbenzofuran derivatives as defined in claim 1 and their physiologically acceptable salts for the preparation of a medicament for the treatment of inflammatory diseases.
3. The use according to claim 2, wherein the inflammatory disease is an inflammatory disease caused by uncontrolled breathing bursts of PMNs.
4. The use according to claim 2, wherein the inflammatory disease is rheumatoid arthritis, compensatory anti-inflammatory response syndrome and 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 |
| CN107586284A (en) * | 2016-07-06 | 2018-01-16 | 中国药科大学 | A kind of purposes of 2 arylbenzofuran analog derivative in gout medicine is prepared |
| CN110183413A (en) * | 2019-07-25 | 2019-08-30 | 江西中医药大学 | Diphenylethylene compounds in two color jackfruits and its purposes in preparation treatment diseases associated with inflammation drug |
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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 |
| CN107586284A (en) * | 2016-07-06 | 2018-01-16 | 中国药科大学 | A kind of purposes of 2 arylbenzofuran analog derivative in gout medicine is prepared |
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