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Guaialactone compound as well as preparation method and application thereof

A technology of ester compound and guaiac, which is applied in the field of guaiac lactone compound and its preparation, and achieves the effect of novel structure and strong inhibitory effect in vitro

Pending Publication Date: 2021-12-31
HUBEI UNIV OF EDUCATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, there are few literature reports on the chemical components and pharmacological activities of Chrysanthemum chrysanthemum, an important close relative of the origin of chrysanthemum, especially the antitumor activity. In order to further study the chemical composition of chrysanthemum, look for natural products with novel structures

Method used

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  • Guaialactone compound as well as preparation method and application thereof
  • Guaialactone compound as well as preparation method and application thereof
  • Guaialactone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Instruments and materials:

[0029] AV-400 MHz superconducting nuclear magnetic resonance instrument (Bruker, Germany); SolariX 7.0T high-resolution Fourier transform mass spectrometer (Bruker, Germany); Nicolet iS50R Fourier transform infrared spectrometer (ThermoScientific, USA); 2535 preparative high-efficiency Liquid chromatograph (Waters, USA); HPLC column XBridgeTM Prep C18 column (250 mm×19 mm, 5 μm) (Waters, USA); 1260 analytical high performance liquid chromatography (Agilent, USA); Analytical HPLC column XBridgeTM Prep C18 column (250 mm × 4.6 mm, 5 μm) (Waters, USA); Milli-Q Integral 5 pure water instrument (Merck Millipore, Germany); R-210 rotary evaporator ( Swiss Büchi Company); miVac Quattro Vacuum Centrifugal Concentrator (GeneVac, UK); Deuterium Reagent: CDCl3 (CIL, USA); Chromatographically Pure Methanol (Thermo Fisher Scientific, USA); Chromatographically Pure Tetrahydrofuran (Shanghai Xingke High Purity Solvent Co., Ltd. company); Sephadex LH-20 dex...

Embodiment 2

[0041] Structural identification of compound 1 and compound 2:

[0042] Compound 1: White needle-like crystal, easily soluble in chloroform. IR (KBr, cm -1 ) vmax: 2922, 1764, 1748, 1693, 1616, 1228, 1153, 1031, 959; HR-ESI-MS shows that the molecular formula is C 17 h 20 o 5 (calcd.forC 17 h 20 NaO 5 [M+Na] + 327.12029, found327.12017), with an unsaturation of 8. 13CNMR and DEPT spectra show that the compound structure contains 17 carbon signals, including 3 CH 3 , 2 CH 2 , 7 CHs and 5 Cs (see Table 1). The γ-lactone (1764cm -1 ), α, β-unsaturated carbonyl (1693cm -1 ) and double bond (1616cm -1 ) characteristic signal. 1 The two doublet signals shown in the HNMR spectrum [δ H 6.35 (1H, d, J=3.4Hz)] and [δ H 5.84 (1H, d, J=3.4Hz)] is the characteristic absorption peak of methylene hydrogen outside the ring of α-methylene-γ-sesquiterpene lactone. 1HNMR spectrum also shows a doublet methyl hydrogen [δ H 0.95 (3H, d, J=7.6Hz)], a vinyl methyl hydrogen [δ H 2.3...

Embodiment 3

[0049] Biological activity test of compound 1 and compound 2:

[0050] MTT method was used to test the effect of compounds 1 and 2 on the proliferation of human liver cancer cell line HepG2, and cisplatin was used as a positive control.

[0051] The specific test method is: in a 10cm culture dish, culture the cells to the logarithmic growth phase, digest with 1mL trypsin and centrifuge to collect the cells, count the cells on a cell counting plate and dilute the cells to 5×10 4 cells / mL, inoculated into 96-well plate, 100 μL per well, cultured overnight at 37°C in a 5% CO2 incubator, and then added to each well the sample to be tested diluted with the medium to 2 times the final concentration, so that the final concentrations of the drugs were respectively 6.25, 12.5, 25, 50 and 100 μmol L -1 , set 4 duplicate wells for each concentration, and after continuing to culture for 24 hours, add 20 μL of MTT solution (0.5% MTT) to each well, and continue to cultivate for 4 hours. A...

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Abstract

The invention discloses a guaialactone compound and a preparation method and application thereof, and relates to the technical field of compound extraction. The guaialactone compound has the following structure. According to the present invention, the chemical components of the chloroform part of Chrysanthemum vestitum are separated and purified through chromatographic methods such as extraction, Diaion HP-20 column chromatography, silica gel column chromatography, Sephadex LH-20 sephadex column chromatography and preparative high performance liquid chromatography to prepare two guailactone derivatives, namely, a compound 1 and a compound 2. The compounds have a novel structure, have strong in-vitro inhibition effect on HepG2 cell strains, and can be used for preparing anti-tumor drugs.

Description

technical field [0001] The invention relates to the technical field of compound extraction, in particular to a guaiacolide compound and its preparation method and application. Background technique [0002] Maohua chrysanthemum is a plant of the genus Chrysanthemum in the Asteraceae family. It grows in Henan, Hubei, Anhui and other places at an altitude of 340-1500 meters on low mountain slopes and hills. Its flowers are used as medicine or as a tea substitute, and have the effect of clearing away heat and detoxifying. Maohua chrysanthemum is an important relative species involved in the origin of chrysanthemum. As a traditional Chinese herbal medicine, chrysanthemum has the functions of dispelling wind and clearing heat, calming liver and improving eyesight, clearing away heat and detoxifying, and its main medicinal ingredients are flavonoids, volatile oil and phenylpropanoids Compounds, etc. Modern pharmacological studies have shown that chrysanthemum has anti-oxidant, anti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93A61P35/00
CPCC07D307/93A61P35/00Y02A50/30
Inventor 王艳丽张洪权董馨语何可欣向涛李娜
Owner HUBEI UNIV OF EDUCATION
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