CN111484485A - Anti-inflammatory macrocyclic polyamine alkaloid celacarfurine - Google Patents
Anti-inflammatory macrocyclic polyamine alkaloid celacarfurine Download PDFInfo
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Abstract
The invention relates to the field of natural medicines and discloses a medicine prepared from tripterygium wilfordii (tripterygium wilfordii)Tripteryginum Wilfordiihook.F) and the structure, separation, identification and application in preparing anti-inflammatory drugs.
Description
Technical Field
The invention belongs to the field of natural medicines, and relates to an anti-inflammatory macrocyclic polyamine alkaloid celacarfurine separated and identified from tripterygium wilfordii.
Background
Tripterygium wilfordii hook (B)Tripteryginum WilfordiiHook, F) is a plant of the genus Leptospermum of the family Celastraceae, and Tripterygium wilfordii is bitter in taste, pungent in nature, cool in nature and toxic in nature according to records of the national Chinese herbal medicine compilation. Has the functions of dispelling wind, detoxicating and killing pests. The external application is used for treating rheumatic arthritis and skin itching, killing maggots and wigglers, killing oncomelania and poisoning rats. It is used for treating intractable immune hyperfunction diseases such as rheumatoid arthritis, chronic nephritis, lupus erythematosus, etc. The main chemical components of tripterygium wilfordii reported at present comprise diterpene, triterpene, alkaloid and the like, wherein the alkaloid components mainly comprise sesquiterpene alkaloid and macrocyclic polyamine alkaloid, wherein the sesquiterpene alkaloid accounts for the majority, and the macrocyclic polyamine alkaloid is rarely reported. In order to discover a new active ingredient from tripterygium wilfordii, the inventor conducts chemical ingredient research on the tripterygium wilfordii, combines with anti-inflammatory drug effect screening, and separates and identifies a new macrocyclic polyamine alkaloid, namely, celacarfurine from the tripterygium wilfordii. The invention discloses a structure of celacarfurine for the first time,Separation and identification and application in preparing anti-inflammatory drugs.
Disclosure of Invention
The invention relates to a novel anti-inflammatory macrocyclic polyamine alkaloid extracted, separated and identified from tripterygium wilfordii, which has the chemical name of (2R) -9-furyl-2-phenyl-1, 5, 9-triazacyclodecanone-4, 13-dione and is named as celacarfurine, and the chemical structure is shown as the following formula I.
Formula I: a celacarfurine structure.
The invention is innovative: 1. compared with the reported macrocyclic polyamine alkaloid, the celacarfurine is the firstly reported macrocyclic polyamine alkaloid with two carbonyl oxidation groups on a 13-membered ring mother nucleus; 2. the celacarfurine is macrocyclic polyamine alkaloid with R configuration at C-2 position on 13-membered ring mother nucleus reported for the first time, and has novel structural characteristics; 3. the anti-inflammatory activity of the macrocyclic polyamine alkaloid is reported for the first time, and the structure, the separation and the identification of the celacarfurine and the application of the celacarfurine in preparing anti-inflammatory drugs are disclosed for the first time.
The invention is realized by the following technical scheme.
Firstly, extraction and separation
1. Slicing radix Tripterygii Wilfordii, adding 95% ethanol water solution, heating and reflux-extracting for 3 times, mixing extractive solutions, concentrating under reduced pressure, and recovering ethanol to obtain total extract. Dissolving the total extract with ethyl acetate for several times, mixing ethyl acetate solutions, concentrating under reduced pressure, and recovering ethyl acetate to obtain ethyl acetate fraction.
2. Subjecting ethyl acetate fraction to neutral alumina chromatography, separating with petroleum ether-ethyl acetate (1: 0, 4:1, 3:2, 2:3,V/V) And ethyl acetate-methanol (1: 0, 3:1, 1:1, 0:1,V/V) Gradient elution is carried out in sequence to obtain 8 elution fractions in sequence, ethyl acetate-methanol (1: 0,V/V) And the elution parts are combined with ethyl acetate-methanol (3: 1, V/V) elution parts and then decompressed and concentrated to obtain the elution part of the neutral alumina chromatographic column.
3. Subjecting the eluted part of the neutral alumina chromatographic column to MCI GE L column chromatography, eluting with methanol-water (0: 1, 1:3,1: 1, 3:1, 1:0,V/V) Gradient elution is carried out in sequence to obtain 5 elution fractions in sequence, methanol-water (3: 1,V/V) Concentrating the eluate under reduced pressure, further performing MCI GE L chromatography, gradient-eluting with methanol-water (0: 1, 1:9, 3:7, 1:1, 7:3, 9:1, 1:0, V/V) to obtain 7 eluate fractions, and concentrating the eluate fractions under reduced pressure to obtain MCI GE L chromatographic column eluate fraction.
4. Subjecting the elution part of the MCI GE L chromatographic column to silica gel chromatographic column chromatography, performing gradient elution with petroleum ether-ethyl acetate (1: 0, 1:1.3, 1:3,1: 5, 1:10, 0:1, v/v) and ethyl acetate/methanol (8: 1, 4:1, 1:3,1:0, v/v) to sequentially obtain 11 elution fractions, combining the elution fractions of petroleum ether-ethyl acetate (1: 10, v/v), and concentrating under reduced pressure to obtain the elution part of the silica gel chromatographic column.
5. Separating the silica gel column eluate with preparative HP L C (YMC-Actus ODS-AC)18Column, mobile phase: the ratio of methanol to water is 40:60,V/Vand detecting the wavelength of 210nm) to obtain the compound celecoxurine.
II, structural identification
A compound of formula I (celecoxurine): determining molecular formula of light yellow solid (solvent chloroform) as C according to high resolution mass spectrum (HR-TOF-MS) (shown in figure 1)21H25N3O4([M+H]+Measured value: m/z 384.1919, theoretical calculation: m/z 384.1918; [ M + HCOO]-Measured value: m/z 428.1825, theoretical calculation: m/z 428.1827). Ultraviolet (275 nm, 241 nm) and Nuclear Magnetic Resonance (NMR) spectra show that the structure contains benzene ring and furan ring. Hydrogen nuclear magnetic resonance spectrum (1H-NMR) (see FIG. 2 and Table 1) showed 8 distinct aromatic hydrogen signals: ( H 7.52, 7.32-7.36, 7.32-7.36,8.02, 7.73, 6.66, H-2 ' and 6 ', H-3 ' and 5 ', H-4 ', H-3 ' ', H-5 ' ', H-6 ' '), respectively belonging to a benzene ring and a furan ring. Carbon nuclear magnetic resonance spectrum (13C-NMR) (see FIG. 3 and Table 1) showed 21 carbon signals, assigned to 7 methylene groups, 9 methine groups and 5 methylene groups, respectively, according to HSQC and DEPT spectraQuaternary carbons including 1 benzene ring, 1 furan ring and 3 amide carbonyl groups (C169.33, 169.25, 163.41, C-4, C-13, C-1 "). The unsaturation was calculated to be 11 according to formula, minus the unsaturation of 1 benzene ring, 1 furan ring and 3 amide carbonyl groups, the remaining 1 unsaturation, indicating that 1 ring was also present in the compound. The above evidence suggests that the compounds have a macrocyclic polyamine alkaloid backbone. Comparing the compound with literature (Kuehne P, Guggisberg A, Hesse M. Synthesis and Chiptic Properties, Soft 13-memberd spidimine alkaloids (-) - (S) -celinine, (0) - (S) -celabenzine, (-) - (S) -celaferine, and (+) - (S) -viburnine [ J ])]Spectroscopic data of (-) - (S) -celafurine of the compound in Helvetica chimica acta, 1997,80(6): 1802- c 169.25 substitution of the (-) - (S) -celafurine Compound by the Low-field amide carbonyl carbon Signal c 59.51 high field methylene carbon signal, indicating that the compound has a structure similar to (-) - (S) -celafurine but with one more amide carbonyl group on the macrocycle, i.e., the C at position 13 of the macrocycle is oxidized. In HMBC spectra, H-2 ( H 5.57, m) /C-2’, 6’ ( C 127.66 and H-2 ', 6' ((R)) H 7.52, dd)/C-2 ( C 73.65) indicates that the phenyl group is located at the C-2 position of the macrocycle. H-8 ( H 3.51, m；2.82, m) /C-1’’ ( C 163.41 and H-10 (C) H 3.68, m; 2.90, m)/C-1’’ ( C 163.41) indicating that the furoyl group is located at the C-9 position of the macrocycle. H-2 (a) H 5.57, m) /C-4( C 169.33 and H-6 (C) H 3.46, m)/C-4 ( C 169.33) indicates that one amide carbonyl is located at the C-4 position of the macrocycle. H-2 (a) H 5.57, m) /C-13 ( C 169.25 and H-11 (C) H 2.09, m)/C-13 ( C 169.25) indicating that another amide carbonyl is located at the C-13 position of the macrocycle. In contrast to (-) - (S) -celafurine, formulaThe compound I shows positive optical rotation value ([ α ]]D 20= 5.78), and the CD profile is also in contrast to (-) - (S) -celafurine, the compounds of formula I exhibit a positive Cotton effect between 200 and 220 nm. This illustrates that the chiral carbon configuration at the C-2 position of the compound of formula I is opposite to that of (-) - (S) -celafurine, i.e., the R configuration. In conclusion, the compound of the formula I is identified as (2R) -9-furyl-2-phenyl-1, 5, 9-triazacyclotide-4, 13-dione, named as celacarfurine, which is determined to be a novel compound by examining the literature.
Formula II: key HMBC associated with celacarfurine.
Synthesis of1H-NMR、13C-NMR, HSQC and HMBC spectra, and the carbon and hydrogen nuclear magnetic signal assignments of celacarfurine are shown in Table 1.
TABLE 1 of celacarfurine1H-NMR and13C-NMR data (600MHz, solvent CD)3OD)
Thirdly, evaluation of anti-inflammatory pharmacodynamics
The invention carries out anti-inflammatory pharmacodynamic evaluation on the celacarfurine.
1. Experiment on the effect of celacarfurine on lipopolysaccharide (L PS) -induced overexpression of primary fibroblast inflammatory factor interleukin 1 β (I L-1 β) in rat knee joint synovium.
1.1 culture of Primary fibroblasts from rat Knee Joint synovium
Male SD rats (180-220 g) are killed after ether anesthesia, knee joint synovial tissues are taken out after being soaked in 75% alcohol for 15-20 minutes, the synovial tissues of the knee joints are cut into pieces, II type collagenase (4 mg/ml) is used for digesting for 2 hours, RPMI Medium 1640 containing 10% fetal bovine serum is added for culturing, cells slowly climb out after about 3 days, after the cells grow to a fusion state, 0.25% pancreatin (containing 0.1% EDTA) is used for digesting for 2 minutes, the cells are continuously cultured for passage, and the primary cells are replaced by 3-6 in the following experiments.
1.2 determination of the Effect of celecarfurine on L PS-induced expression of primary fibroblast cells of knee synovium I L-1 β
The celacarfurine was dissolved in DMSO at a stock concentration of 10mM and diluted to 1mM in Phosphate Buffered Saline (PBS) immediately before use at a final concentration of 10. mu.M. the cells were washed with 2 × 106The seeds were plated in 48-well plates at 37 ℃ in 5% CO2Culturing under the condition of 80% fusion state, washing twice with PBS, changing to serum-free culture medium, adding celacarfurine solution to make final concentration be 10 μ M, after 0.5 hr, adding L PS (10 ng/ml) as stimulant, dividing experiment into blank group, model group, celacarfurine administration group, positive control prednisolone administration group (final concentration of experiment is 10 μ M), modeling model group with L PS (10 ng/ml) as stimulant, adding corresponding compound into administration group, 6 re-wells for each group, 37 deg.C, 5% CO2After 24 hours of incubation under the conditions, OD was measured at a wavelength of 450nm as required by the rat I L-1 β E L ISA kit.
1.3 results of the experiment
The results show (see table 2) that the expression of the model group I L-1 β is greatly increased (P < 0.001) compared with that of the blank group, which indicates that the modeling is successful, the administration group of the celacarfurine and the prednisolone have very significant difference (P < 0.001), which indicates that the celacarfurine can obviously inhibit the excessive expression of the L PS-induced primary fibroblast inflammatory factor I L-1 β of the synovial membrane of the knee joint, the inhibition effect is better than that of the positive drug prednisolone, and the celacarfurine has obvious anti-inflammatory activity.
TABLE 2 Effect of celecarfurine on L PS-induced synovial primary fibroblast I L-1 β expression (mean X + -S, n =6)
Comparison with model group P < 0.001.
2. Experiment for influence of celacarfurine on mouse ear swelling model caused by dimethylbenzene
The celecoxurine was dissolved in 2% aqueous propylene glycol. The Kunming mouse with the weight of 18-22g and half of the male and female is randomly divided into a model group, a celacarfurine administration group and a positive control drug indometacin administration group, wherein each group comprises 10 mice. Each administration group was gavaged at a dose of 10mg/kg, and the model group was given an equal volume of 2% propylene glycol aqueous solution. The administration was continued for 3 days, 1 hour after the last administration, and 20. mu.l of xylene was applied to both sides of the right auricle of the mouse to cause inflammation, while the left auricle was not applied as a control. After 1 hour, the mice were sacrificed, both ears were cut off, round ears were punched out of the same portions with a punch having a diameter of 6mm, respectively, and weighed. The inhibition rate was calculated by taking the difference in the weight of the left and right ear pieces as the degree of swelling. The experimental results are shown in table 3, the average ear swelling degree of each administration group is significantly different (P <0.01) compared with that of a model group, the inhibition rate of the celecoxurine is 55.3%, and the inhibition rate is higher than that of the positive drug indometacin. The experimental result shows that the celacarfurine has obvious anti-inflammatory activity and is superior to the positive drug indometacin.
TABLE 3 Effect of celecoxurine on xylene-induced ear swelling model in mice (mean X + -S, n =10)
P <0.01 compared to model group.
Preparation of anti-inflammatory medicinal preparation
The celacarfurine or the pharmaceutical composition taking the celacarfurine as the basic activity can be combined with pharmaceutically suitable auxiliary materials or carriers and prepared into preparations such as injections, tablets, capsules, dropping pills, controlled release preparations, sustained release preparations, nano preparations and the like.
Drawings
FIG. 1 is a graph of HR-TOF-MS (positive ion mode) spectrum of celecoxurine.
FIG. 2 is a drawing of celecoxurine1H-NMR spectrum.
FIG. 3 is a drawing of celecoxurine13C-NMR spectrum.
FIG. 4 is an HSQC spectrum of celecoxurine.
FIG. 5 is an HMBC spectrum of celecoxurine.
FIG. 6 is a CD spectrum of celecoxurine.
Detailed Description
The following examples are further described, but the present invention is not limited to the scope of the examples.
Example 1:
119 Kg of dried roots of tripterygium wilfordii are sliced, 400 liters of 95 percent ethanol is added, the mixture is heated and refluxed for extraction for 3 times (1.5 × 1.5 for 1.5 × 1 hours) at 70 ℃, the extracting solutions are merged, the solvent is recovered by decompression concentration, the extract 12 Kg. is obtained, the extract is dissolved by ethyl acetate for a plurality of times, the ethyl acetate solution is merged, and the solvent is recovered by decompression concentration, so that 1.87Kg of ethyl acetate parts are obtained.
Subjecting the ethyl acetate part extract 1.87Kg to neutral alumina column chromatography (200 meshes, 300 meshes, 22.5 Kg), petroleum ether-ethyl acetate (1: 0, 4:1, 3:2, 2:3,V/V) And ethyl acetate-methanol (1: 0, 3:1, 1:1, 0:1,V/V) Gradient elution, collecting 50L from each fraction, sequentially obtaining 8 elution fractions (Fr.1-Fr.8), combining Fr.5 and Fr.6 fractions, and concentrating to obtain Fr.56 fraction (142.2 g).
Fr.56 fractions were separated on MCI GE L-CHP 20P column, eluted with methanol/water (0: 1, 1:3,1: 1, 3:1, 1:0, v/v) gradient to give 5 fractions (Fr.56.1-Fr.56.5), Fr.56.4 fractions (52.92 g) on MCI GE L-CHP 20P column, and eluted with methanol/water (0: 1, 1:9, 3:7, 1:1, 7:3, 9:1, 1:0, v/v) gradient to give 7 fractions (Fr.56.4.1-Fr.56.4.7).
Fr.56.4.4.4 fractions (8 g) were chromatographed on silica gel (200-mesh 300 mesh, 240 g) column with petroleum ether/ethyl acetate (1: 0, 1:1.3, 1:3,1: 5, 1:10, 0:1, v/v) and ethyl acetate/methanol (8: 1, 4:1, 1:3,1:0, v/v) in a gradient manner to give 11 fractions (Fr.56.4.4.1-Fr.56.4.4.11).
Fr.56.4.4.5 fractions were separated by preparative HP L C (YMC-Actus ODS-AC18 column, mobile phase: methanol/water 40:60, detection wavelength 210nm) to give the compound celecoxurine.
Example 2:
preparation of a celacarfurine tablet: mixing 25mg of the compound with 25mg of starch and 25mg of dextrin, wetting with a proper amount of 30% ethanol, conventionally granulating, adding a proper amount of magnesium stearate, mixing, and tabletting to obtain the compound.
Example 3:
preparation of a celacarfurine capsule: mixing 25mg of the compound with 60mg of starch, 10mg of dextrin and 10mg of powdered sugar, moistening with an appropriate amount of 30% ethanol, conventionally granulating, and filling into hard capsules.
Claims (3)
1. A macrocyclic polyamine alkaloid having the structure shown in formula I below, designated as celacarfurine:
formula I.
2. The preparation process of the macrocyclic polyamine alkaloid celacarfurine as claimed in claim 1 comprises slicing radix Tripterygii Wilfordii, adding 95% ethanol water solution, heating and refluxing for 3 times, combining the extractive solutions, concentrating under reduced pressure to recover ethanol to obtain total extract, dissolving the total extract with ethyl acetate for several times until the total extract is not dissolved, combining the ethyl acetate solutions, concentrating under reduced pressure to recover ethyl acetate to obtain ethyl acetate fraction, subjecting the ethyl acetate fraction to neutral alumina chromatographic column chromatography, subjecting the ethyl acetate fraction to gradient elution with petroleum ether-ethyl acetate and ethyl acetate-methanol in sequence, combining the ethyl acetate-methanol with a volume ratio of 1:0 and the ethyl acetate-methanol eluate fraction with a volume ratio of 3:1, concentrating under reduced pressure to obtain neutral alumina chromatographic column eluate fraction, subjecting the neutral alumina chromatographic column eluate fraction to MCIGE L chromatographic column chromatography, subjecting the neutral alumina chromatographic column eluate fraction to gradient elution with methanol-water in sequence, subjecting the methanol-water eluate fraction with a volume ratio of 3:1 to gradient elution, subjecting the methanol-water eluate fraction to gradient elution with methanol-water, subjecting the methanol-water eluate fraction with a methanol-water gradient elution fraction of 3:1, concentrating under reduced pressure to obtain MCGE chromatographic column chromatography, subjecting the methanol-HP eluate fraction to obtain petroleum ether fraction, subjecting the petroleum ether gradient chromatography, subjecting the MCGE chromatographic fraction to gradient elution fraction to separation to obtain MCGE chromatographic column chromatography, and subjecting the petroleum ether fraction to silica gel fraction.
3. Use of the macrocyclic polyamine alkaloid, celacarfurine, as defined in claim 1 in the preparation of an anti-inflammatory agent.
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| CN112574182A (en) * | 2020-10-12 | 2021-03-30 | 江西中医药大学 | Effective part of tripterygium wilfordii macrocyclic polyamine alkaloid and preparation method thereof |
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