CN110627644B - Capsinoid compound, pharmaceutically acceptable salt thereof, and preparation method and application thereof - Google Patents
Capsinoid compound, pharmaceutically acceptable salt thereof, and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a capsinoid compound, a pharmaceutically acceptable salt thereof, a preparation method and an application thereof. The structure of the capsinoid compound is reported for the first time, and the capsinoid compound is derived from caulis spatholobi and can be used as a standard substance for identifying capsinoid substances in the caulis spatholobi. The capsaicine ester compound provided by the invention is separated from the ethyl acetate extract of the quality caulis Spatholobi, and surprisingly, the compound is also found to have good analgesic effect and is expected to be used as an analgesic drug.
Description
Technical Field
The invention belongs to the field of natural phytochemistry, and particularly relates to a capsaicine ester compound obtained from caulis spatholobi, and a preparation method and application thereof.
Background
Compared with the capsaicin compounds, the capsaicin ester compounds have no pungent taste and cell activity of the capsaicin compounds, so the capsaicin ester compounds have better application value. Known researches show that the traditional Chinese medicine composition has the effects of enhancing the immune system, promoting fat metabolism, inhibiting obesity, relieving pain and the like. CN1791400A discloses that it has the effect of reducing the total serum cholesterol level and improving the arteriosclerosis index of a subject. Although the capsinoid compounds have received enough attention, the synthesis thereof has certain difficulties and the study on the activity thereof is still not thorough, and thus, the researches are still under intensive study.
Caulis Spatholobi is the dried rattan of Spatholobus Suffruticosa of Leguminosae, and the chemical components of caulis Spatholobi include flavonoids, lignans, terpenes, sterols, anthraquinones, phenolic acids and glycosides thereof. Despite the knowledge of a few large classes, researchers have been able to isolate new compounds in increasingly advanced extraction processes, some of which have been studied to find that they are more active in certain respects than compounds known to have similar structures, helping chemists to explore new pharmaceuticals, agricultural or other chemicals.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a capsaicine ester compound. The structure of the capsinoid compound is reported for the first time, and the capsinoid compound is derived from caulis spatholobi and can be used as a standard substance for identifying capsinoid substances in the caulis spatholobi. Surprisingly, the capsaicine ester compound also shows good analgesic performance and is expected to be used for preparing or developing new analgesic drugs.
The invention also aims to provide a preparation method of the capsaicine ester compound.
The invention also aims to provide application of the capsaicine ester compound.
The above object of the present invention is achieved by the following technical solutions:
a capsinoid compound and a pharmaceutically acceptable salt thereof, wherein the capsinoid compound has a structural formula shown as a formula (I):
the pharmaceutically acceptable salt of the capsaicine ester compound has a structural formula shown as a formula (II):
m is an alkali metal or an alkaline earth metal, and n is 1 or 2.
The capsinoid compound is found for the first time and can be named as 4-oxo-nonanoic acid homovanillic ester; it can be used as standard substance for identifying capsaicine ester in caulis Spatholobi.
In the present application, the alkali metal is selected from potassium, sodium, lithium; the alkaline earth metal is selected from calcium, magnesium and barium.
The preparation method of the capsaicine ester compound comprises the following steps:
s1, adding water into a caulis spatholobi certified medicinal material, performing reflux extraction, concentrating, and drying to obtain a caulis spatholobi dry extract;
s2, dissolving the caulis Spatholobi dry extract obtained in the step S1 with water, and extracting with ethyl acetate to obtain an ethyl acetate extract;
s3, chloroform is used: eluting S2 on a silica gel column by using a system with the methanol volume ratio of (70-90): 1, and obtaining an ethyl acetate extract to obtain a component Fr.1;
s4.Fr.1 is subjected to silica gel chromatography, chloroform-methanol is sequentially subjected to gradient elution by a ratio system of 60:1, (50-40): 1, (30-20): 1 and 10:1, and a component obtained by collecting the ratio of 10:1 is named as Fr.1-4;
s5.Fr.1-4 is detected by TLC and HPLC, RP-SP-HPLC is adopted to sequentially adopt acetonitrile with the volume ratio of 2:3, 11:9 and 4: 1: eluting in a water system, and collecting components obtained by eluting at a ratio of 4:1, namely Fr.1-4-3, and then adding acetonitrile at a volume ratio of (40-50) to (60-50): combining an aqueous solvent with RP-SP-HPLC to obtain the capsaicine ester compound.
In the invention, the caulis spatholobi certified drug is dried rattan of Spatholobus suberectus Dunn of leguminous plant.
Preferably, in S1, the mass ratio of the caulis spatholobi to water is 1: 5.
Preferably, in s1, the number of extractions is 2.
Preferably, in s1, the concentration is concentration under reduced pressure.
Preferably, in s1, the drying is vacuum drying at 75 ℃.
Preferably, in s2, the number of extractions is 8.
Preferably, in s3, the chloroform-methanol volume ratio is 80: 1.
Preferably, in S4, the gradient elution ratio of chloroform to methanol is 60:1, 40:1, 20; 1. 10; 1.
preferably, TLC tracing is performed while elution is performed by silica gel chromatography with chloroform-methanol at the ratio of 60:1, 40:1, 20:1, 10:1 in this order, and when the eluent obtained with the same ratio of eluent shows a change in composition, the eluent with the next ratio is changed.
Preferably, in s5, the acetonitrile: the volume ratio of the water solvent is 45: 55.
After the capsinoid compound is obtained, a corresponding salt can be obtained by reacting the capsinoid compound with an inorganic base formed from a corresponding alkali metal or alkaline earth metal.
The application also provides a synthetic method of the capsaicine ester compound, which comprises the following steps: 4-oxo-nonanoic acid is subjected to acyl chlorination and then reacts with homovanillic alcohol to obtain the capsaicine ester compound.
More specific reaction conditions are:
dissolving 4-oxo-nonanoic acid and pyridine in a solvent, slowly adding thionyl chloride at the temperature of-2 ℃, transferring to room temperature after dropwise addition, continuously stirring for 1h, heating for reflux, and carrying out TLC detection reaction until acyl chloride reaction is finished.
Preferably, the molar ratio of the 4-oxo-nonanoic acid to the thionyl chloride is 1: 1.5-2.5. More preferably 1: 2.
The solvent is preferably acetone.
The dropping speed is controlled to be over within 1 hour.
The capsinoid compound is applied to a standard substance for detecting the content of capsinoid in caulis spatholobi.
The analgesic effect of the capsaicinoid compound is unexpectedly found to be superior to that of high vanillic pelargonate ester through an analgesic experiment, so that the capsaicinoid compound is expected to be used for preparing or developing a new analgesic drug. Similarly, the pharmaceutically acceptable salt of the capsaicine ester compound is also expected to be used for preparing or developing new analgesic drugs.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a novel capsaicine ester compound and pharmaceutically acceptable salt thereof, wherein the capsaicine ester compound is obtained by extracting and separating caulis spatholobi certified products and can be used as a standard substance for detecting the content of capsaicine substances in caulis spatholobi. The analgesic effect of the capsaicinoid compound is unexpectedly found to be superior to that of high vanillic pelargonate through an analgesic experiment, so that the capsaicinoid compound and the pharmaceutically acceptable salt thereof are expected to be used for preparing or developing new analgesic drugs.
Drawings
FIG. 1 is a mass spectrum of the capsaicinoid compound of the invention.
Detailed Description
The following examples are presented to further illustrate the present invention and should not be construed as limiting the invention. It is within the scope of the present invention to make simple modifications or alterations to the methods, procedures or conditions of the present invention without departing from the spirit and substance of the invention; unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art.
EXAMPLE 1 extraction and isolation of the Compound 4-Oxonanoic homovanillyl ester
The caulis Spatholobi as certified drug was collected from Yunnan in 2016 (3 months) and identified as dried rattan of Leguminosae plant Spatholobus suberectus Dunn. certificate specimens (Y008-1608010) were stored in national focus laboratories of natural medicine and biomimetic medicine of Beijing university college of pharmacy.
Weighing 70kg of dried caulis spatholobi, adding 5 times of water, performing reflux extraction for 2 times, each time for 2 hours, combining extracting solutions, concentrating under reduced pressure, performing vacuum drying for 7 hours at 75 ℃ to obtain 6kg of caulis spatholobi dry extract (the yield is 8.57%), remaining 1kg, dissolving the rest 5kg with 6L of deionized water, sequentially extracting with a proper amount of ethyl acetate for 8 times, respectively combining extracting solutions, concentrating under reduced pressure and drying by distillation to obtain 320g of ethyl acetate extract (the yield is 0.46% calculated according to the raw material charge).
The ethyl acetate extract (270g) was subjected to silica gel column chromatography and eluted with chloroform-methanol system 80:1 to give fraction Fr.1.
Fr.1(19.9g) is subjected to silica gel column chromatography, chloroform-methanol mixed solution of 60:1, 40:1, 20:1 and 10:1 is sequentially used for elution, 3 column volumes are eluted in each gradient, and a component obtained by 10:1 ratio, namely Fr.1-4, is collected;
fr.1-4 is detected by TLC and HPLC, RP-SP-HPLC is adopted to sequentially adopt acetonitrile with the volume ratio of 2:3, 11:9 and 4: 1: eluting a water system, and collecting components eluted by 4:1, namely Fr.1-4-3, and then adding acetonitrile with the volume ratio of 45: 55: and (3) combining an aqueous solvent with RP-SP-HPLC to obtain the capsaicinoid compound (5.6mg, tR ═ 39.1 min).
Example 2
In the extraction and separation process of the compound 4-oxo-nonanoic acid homovanillic alcohol ester, the volume ratio of chloroform to a methanol system in S3. can also be eluted on a silica gel column by 70: 1S 2. the obtained ethyl acetate extract is obtained to obtain a component Fr.1; the other steps were carried out as described in example 1 for the extraction and isolation procedure to obtain the compounds of the present invention.
Example 3
In the extraction and separation process of the compound 4-oxo-nonanoic acid homovanillic alcohol ester, the volume ratio of chloroform to a methanol system in S3. can also be eluted on a silica gel column by 90: 1S 2. the obtained ethyl acetate extract is obtained to obtain a component Fr.1;
the other steps were carried out as described in example 1 for the extraction and isolation procedure to obtain the compounds of the present invention.
Example 4
In the extraction and separation process of the compound 4-oxo-nonanoic acid homovanillic ester, the gradient elution ratio of chloroform to methanol system in S4. can be 60:1, 50:1, 30:1 and 10:1, and other steps are carried out according to the extraction and separation process described in the embodiment 1, so as to obtain the compound.
EXAMPLE 5 structural identification of the Compound 4-Oxonanoic homovanillyl ester
The hydrogen spectrum, carbon spectrum and mass spectrum data of the capsaicine ester compound are as follows:
1H-NMR(400MHz,DMSO-d6)δ:6.80(1H,d,J＝1.9Hz,H-2),6.69(1H,d,J＝8.0Hz,H-5),6.60(1H,dd,J＝8.0,1.9Hz,H-6),2.74(2H,t,J＝7.0Hz,H-7),
4.13(2H,t,J＝7.0Hz,H-8),3.74(3H,s,3-OMe),2.44(2H,t,J＝6.7Hz,H-2'),2.66(2H,t,J＝6.7Hz,H-3'),2.39(2H,t,J＝7.4Hz,H-5'),1.45(2H,m,H-6'),1.25(4H,m,H-7',8'),0.85(3H,t,J＝7.1Hz,H-9')。
13C-NMR(100MHz,DMSO-d6)δ:128.6s(C-1),113.2d(C-2),147.6s(C-3),145.3s(C-4),115.5d(C-5),121.1d(C-6),36.7t(C-7),65.0t(C-8),55.7q(3-OMe),172.4s(C-1'),27.8t(C-2'),34.1t(C-3'),209.1s(C-4'),41.8t(C-5'),23.1t(C-6'),30.9t(C-7'),22.1t(C-8'),14.0q(C-9')。
HRESIMS m/z 321.1699[M-H]-(calcd for C18H25O5321.1702) shown in detail in fig. 1.
EXAMPLE 6 Artificial Synthesis method of capsinoid Compound
4-oxo-nonanoic acid (10.00g, 59.46mmol, 1.00eq) and pyridine (23.52g, 5.00eq) are dissolved in 50ml of acetone solution, thionyl chloride (14.18g, 2.00eq) is slowly added dropwise under stirring at-2 ℃ within 1h, then the solution is transferred to room temperature and stirred for 1h, heated and refluxed, and the reaction is monitored by a TLC plate until the acyl chlorination reaction is completed. Adding homovanillic alcohol (10.24g, 1.00eq) into a reaction system, reacting for 4h at 30-35 ℃, adding 100ml of deionized water and 100ml of ethyl acetate after the reaction is finished, extracting twice, combining organic layers, drying by anhydrous sodium sulfate, and performing rotary evaporation to obtain the capsaicine ester compound (16.57g, 86.44%). The compound was confirmed by mass spectrometry and hydrogen spectrometry to be identical to the compound isolated in example 1.
Analgesic test of 4-oxononanoic acid homovanillyl ester compound
The acetic acid writhing experiment is a classical model of peripheral analgesia, which is caused by mouse peritoneal inflammation caused by acetic acid stimulation and is one of methods for evaluating and screening analgesics. Acetic acid with a certain volume and concentration is injected into the abdominal cavity of a mouse to stimulate the visceral layer and parietal peritoneum to cause inflammatory pain with a large deep part and a long time, so that the mouse has behavioral reactions such as abdominal indent, trunk and hind limb stretch, hip rising and the like, which are called writhing reaction. The frequency of the reaction is high within 15min after injection, so the number of writhing times or the number of mice which react within 15min after injection is taken as the quantitative index of pain.
Experimental animals: 20 healthy adult male and female mice are randomly divided into 8 groups, and each group comprises 5 mice, namely a model control group (normal saline) and a positive control group (aspirin, 20 mg/kg); a control compound high dose group (vanilloid pelargonate, 1.0mg/kg), a control compound medium dose group (vanilloid pelargonate, 0.5mg/kg), a control compound low dose group (vanilloid pelargonate, 0.1mg/kg), a compound high dose group (1.0mg/kg), a compound medium dose group (0.5mg/kg), and a compound low dose group (0.1 mg/kg).
The compound is the 4-oxo-nonanoic acid homovanillic alcohol ester compound.
The chemical stimulus acetic acid solution 2.0% (0.1mL/10g) was intraperitoneally injected 60 minutes after the administration for each group, the number of writhing of the mice within 15min after the acetic acid injection was recorded, and the analgesic effect of the drug was judged, and the results are shown in Table 1.
TABLE 1
| Group of | Dosage form | Mean number of wriggling within 15min |
| Model control group | / | 107.4±3.65 |
| Positive control group | 20 | 55.4±4.04a |
| Low dose group of control Compound | 0.1 | 105±7.68 |
| Dose groups in control Compounds | 0.5 | 95±5.61a |
| High dose group of contrast compounds | 1.0 | 79±4.95a |
| Compound low dose group | 0.1 | 94.8±5.40ab |
| Compound middle dose group | 0.5 | 75.2±4.76ab |
| High dose group of compounds | 1.0 | 67.6±4.28ab |
a: there was a very significant difference p <0.001 from the model control group, b: a significant difference p <0.05 compared to an equivalent dose of the comparative compound;
the experimental results show that: compared with a model control group, the capsaicin ester compounds have analgesic effect except for a low-dose group of the comparison compound, and further have better analgesic effect compared with the comparison compound.
Claims (7)
1. A preparation method of capsinoid compounds is disclosed, wherein the capsinoid compounds have a structural formula shown in formula (I):
the method is characterized by comprising the following steps:
s1, adding water into a caulis spatholobi certified medicinal material, performing reflux extraction, concentrating, and drying to obtain a caulis spatholobi dry extract;
s2, dissolving the caulis Spatholobi dry extract obtained in the step S1 with water, and extracting with ethyl acetate to obtain an ethyl acetate extract;
s3, chloroform is used: eluting S2 on a silica gel column by using a system with the methanol volume ratio of (70-90): 1, and obtaining an ethyl acetate extract to obtain a component Fr.1;
s4.Fr.1 is subjected to silica gel chromatography, chloroform-methanol is sequentially subjected to gradient elution by a ratio system of 60:1, (50-40): 1, (30-20): 1 and 10:1, and a component obtained by collecting the ratio of 10:1 is named as Fr.1-4;
s5.Fr.1-4 is detected by TLC and HPLC, RP-SP-HPLC is adopted to sequentially adopt acetonitrile with the volume ratio of 2:3, 11:9 and 4: 1: eluting in a water system, and collecting components obtained by eluting at a ratio of 4:1, namely Fr.1-4-3, wherein the Fr.1-4-3 is subjected to acetonitrile treatment in a volume ratio of (40-50) to (60-50): and (3) combining an aqueous solvent with RP-SP-HPLC to obtain the capsaicinoid compound.
2. The preparation method according to claim 1, wherein in S1, the mass ratio of the caulis Spatholobi to water is 1: 5.
3. The method according to claim 1, wherein in S1, the number of times of extraction is 2, and the concentration is concentration under reduced pressure.
4. The method according to claim 1, wherein in S1, the drying is vacuum drying at 75 ℃.
5. The method according to claim 1, wherein, in S2, the number of times of extraction is 8.
6. The preparation method according to claim 1, wherein in S4, the gradient elution ratio of chloroform to methanol is 60:1, 40:1, 20:1, 10: 1.
7. The application of the capsaicinoid compound in serving as a standard substance for detecting the content of capsaicinoid in caulis spatholobi;
the capsaicine ester compound has a structural formula shown in a formula (I):
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| 辣椒素生物合成路径及调控基因研究的最新进展;成善汉等;《分子植物育种》;20081231;第6卷(第2期);第335-340 页 * |
| 高通量筛选辣椒素与辣椒素酯生物活性的初步研究;董新荣等;《中国食品学报》;20090430;第9卷(第2期);第5-10页 * |
| 鸡血藤中的酚酸类化合物;瞿璐等;《热带亚热带植物学报》;20141231;第22卷(第3期);第301-306页 * |
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