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Reagent and method for determining total amount of sesquiterpene lactone containing alpha, beta-unsaturated ketone in feverfew

A sesquiterpene lactone, unsaturated technique for use in pharmaceutical analysis

Pending Publication Date: 2021-09-21
SICHUAN ACAD OF CHINESE MEDICINE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the lack of corresponding commercially available reference substances, the content of other sesquiterpene lactones containing α,β-unsaturated ketones in feverfew has rarely been reported.

Method used

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  • Reagent and method for determining total amount of sesquiterpene lactone containing alpha, beta-unsaturated ketone in feverfew
  • Reagent and method for determining total amount of sesquiterpene lactone containing alpha, beta-unsaturated ketone in feverfew
  • Reagent and method for determining total amount of sesquiterpene lactone containing alpha, beta-unsaturated ketone in feverfew

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of 4-chloro-N-(2-mercaptoethyl)benzamide

[0038] In dichloromethane (30ml) at 0°C, 4-chlorobenzoyl chloride (1.00g, 5.71mmol) was slowly added, followed by β-mercaptoethylamine (0.45g, 5.86mmol), and heated under reflux for 2 hours. The reaction solution was washed with saturated sodium bicarbonate (10mL) and concentrated brine (10mL) accordingly, Na 2 SO 4 Dry and concentrate under reduced pressure to a yellowish solid. After repeated crystallization from a mixed solvent of n-hexane-dichloromethane (1:1, v / v), a white solid (0.62 g, yield 50.3%) was obtained. ESI-MS: m / z 214.0087[M-H] - (calculated m / z 214.0093, C 9 h 9 ClNOS); 1 H NMR (600MHz, CDCl 3 )δ7.64 (2H, d, J = 8.6Hz), 7.31 (2H, d, J = 8.6Hz), 6.80 (1H, br s), 3.53 (2H, d, J = 6.4Hz), 2.69 (2H ,dt,J=8.4Hz,6.4Hz),1.38(H,t,J=8.4Hz); 13 C NMR (150MHz, CDCl3) δ166.6, 137.9, 132.6, 128.7, 128.4, 42.9, 24.6, among which, the hydrogen and carbon spectra are shown in figure 2 and image 3 .

Embodiment 2

[0040] The detection method of 4-chloro-N-(2-mercaptoethyl)benzamide

[0041] Using ACQUITYUPLC ultra-high performance liquid chromatography, the chromatographic conditions are chromatographic column Waters BEH C18 (50×2.1mm, 1.7μm), mobile phase acetonitrile-water (35:65, v / v), flow rate 0.4mL / min, column temperature 35°C, detection wavelength 238nm, see attached chromatogram figure 1 . Under this condition, the regression equation of 4-chloro-N-(2-mercaptoethyl) benzamide is y=2284.6x-1474.9(R 2 =0.9999), y is the peak area, x is the concentration (μM) of 4-chloro-N-(2-mercaptoethyl) benzamide, R 2 is the correlation coefficient, the linear range is 2.5-200μM.

Embodiment 3

[0043] Establishment of Calibration Curve

[0044]Take an appropriate amount of parthenolide, weigh it accurately, dissolve it in a phosphate buffer (10mM, pH7.4)-methanol mixed solution (1:1, v / v), and prepare the concentration of 10, 20, 60, 80, 100, 150, 200μM Serial reference solution. Take an appropriate amount of 4-chloro-N-(2-mercaptoethyl)benzamide, accurately weigh it, dissolve it in a mixed solution of phosphate buffer (10mM, pH7.4)-methanol (1:1, v / v), and prepare into a solution with a concentration of 200 μM. Parthenolide solutions of different concentrations were mixed with an equal volume of 4-chloro-N-(2-mercaptoethyl)benzamide solution respectively, and reacted at 37°C for 120 minutes. Detect the remaining amount of 4-chloro-N-(2-mercaptoethyl)benzamide in the solution after 120 minutes of reaction, and calculate its clearance rate. With the concentration of parthenolide in the initial reaction solution as abscissa, with the clearance rate of 4-chloro-N-(2-...

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Abstract

The invention discloses a reagent and method for determining the total amount of sesquiterpene lactones containing alpha, beta-unsaturated ketones in feverfew, and belongs to the technical field of pharmaceutical analysis. The detection reagent is 4-chloro-N-(2-mercaptoethyl) benzamide. The detection method comprises the following steps of: reacting a feverfew extracting solution with 4-chloro-N-(2-mercaptoethyl) benzamide under set conditions for a certain time; detecting the residual amount of the 4-chloro-N-(2-mercaptoethyl) benzamide in the reaction solution; and calculating to obtain the total amount of the sesquiterpene lactone containing the alpha, beta-unsaturated ketone in the feverfew. The method does not depend on a reference substance of a detected compound, and a simple and easy analysis method is provided for determining the total amount of the sesquiterpene lactone containing the alpha, beta-unsaturated ketone in the feverfew.

Description

technical field [0001] The invention relates to a method for determining the total amount of sesquiterpene lactones containing α,β-unsaturated ketones in feverfew, belonging to the technical field of drug analysis. Background technique [0002] Feverfew, also known as Short Tongue Piju [Tanacetum parthenium (L.) Schultz Bip.] is a kind of Compositae medicinal plant originating in Europe. Studies have shown that feverfew contains a variety of sesquiterpene lactones, most of which have anti-inflammatory, anti-tumor and immune regulation effects. The common feature of these components is that they have structural fragments of α, β-unsaturated ketones, which enable them to covalently bind to cysteine ​​residues of certain proteins in the body, thereby regulating the function of the protein. Sesquiterpene lactones are considered to be the most important group of medicinal substances in feverfew, and its representative compound is parthenolide. [0003] The structure of partheno...

Claims

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Application Information

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IPC IPC(8): C07C323/25G01N33/00
CPCC07C323/25G01N33/00
Inventor 陈雏吴燕李彬杜蕾蕾
Owner SICHUAN ACAD OF CHINESE MEDICINE SCI
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