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Lignanoid compound, and preparation method and application thereof

A technology for lignans and compounds, applied in the field of medicine, can solve problems such as no reports, and achieve novel structure, good research and development prospects, and the effects of preventing and treating viral infections.

Inactive Publication Date: 2016-11-09
JIANGSU KANION PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the early stage, in-depth research on the chemical components in Reduning Injection has been carried out, but the main components found are caffeoylquinic acid components and iridoid components, which have been confirmed by in vivo and in vitro experiments. The composition has better antiviral effect, but the new compound disclosed in this patent and its effect of inhibiting influenza A virus H1N1 / H3N2 have not been reported yet

Method used

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  • Lignanoid compound, and preparation method and application thereof
  • Lignanoid compound, and preparation method and application thereof
  • Lignanoid compound, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1, the preparation of compound of the present invention

[0033] (1) Take the finished product of Reduning Injection, separate it through HP-20 macroporous adsorption resin chromatographic column, elute with water, 25~35% ethanol, and 90~100% ethanol in sequence, collect the eluents respectively, and depressurize Concentrate until there is no alcohol smell, and obtain the water elution site, 25-30% ethanol elution site, and 90-100% ethanol elution site;

[0034] (2) Take the part eluted with 90-100% ethanol in step (1), separate it by silica gel column chromatography, and use chloroform-methanol gradient elution to collect 1.8 g of fraction B with a ratio of chloroform-methanol of 95:5. ODS column chromatography, eluted with methanol-water gradient, collected 95 mg of fraction C with a ratio of methanol-water of 6:4, fraction C was separated by semi-preparative liquid chromatography, and acetonitrile-water with a ratio of 30:70 was used as the mobile phase, ...

Embodiment 2

[0035] Embodiment 2, get the compound of the present invention that embodiment 1 makes, carry out following structural identification

[0036] The compound is a yellow amorphous powder, ESI-MS (positive) gives m / z 411 [M+Na] + , ESI-MS(negative) gave m / z 387 [M-H] - , suggesting that the molecular weight of the compound is 388. HR-ESI-Q-TOF-MS gave m / z 411.1422 [M+Na] + (calculated value is 411.1420) (see figure 1 ), confirm that the molecular formula of the compound is C 21 h 24 o 7 , with a calculated unsaturation of 10.

[0037] of this compound 1 H-NMR (400 MHz, in CD 3 OD) spectrum (see figure 2 ), showing 21 hydrogen signals, 4 aromatic hydrogen signals [ δ 6.65 (1H, s, H-2′), 6.64 (1H, d, J =1.6 Hz, H-2), 6.69 (1H,d, J = 8.0 Hz, H-5), 6.40 (1H, dd, J [ δ 3.90 (3H, s), 3.37 (3H, s), 3.77 (3H, s)], suggesting that it may be connected to the benzene ring. 13 C-NMR (100MHz, in CD 3 OD) combined with DEPT-135 profile (see image 3 ) showed a total...

Embodiment 3

[0042] Example 3, the compounds of the present invention are tested against H1N1 and H3N2 in vitro

[0043] 1. Materials

[0044] 1.1 Virus strains Influenza A virus (A / Human / Hubei / 2005 H3N2) and influenza A virus (A / PR / 8 / 34H1N1), passaged and preserved by Wuhan Institute of Virology, Chinese Academy of Sciences;

[0045] 1.2 Cell model The dog kidney cell line MDCK was preserved in our laboratory. Culture conditions: DMEM+10% fetal bovine serum, 37°C, 5% CO2;

[0046] 2. Principles and methods

[0047] 2.1 Drug cytotoxicity detection

[0048] Assay principle: alamarBlue® is a redox indicator that produces an absorbance change and a fluorescent signal according to metabolic activity. AlamarBlue® is easily soluble in water, and its oxidized form enters the cells and is reduced by mitochondrial enzymes to produce measurable fluorescence and color changes, which are used for quantitative analysis of cell viability and cell proliferation and in vitro cytotoxicity studies. Thi...

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Abstract

The invention discloses a lignanoid compound, and a preparation method and an application thereof. The preparation method comprises the following steps: 1, taking a finished Reduning injection product, carrying out HP-20 macroporous adsorption resin column chromatography separation, sequentially carrying out gradient elution with water, 25-35% ethanol and 90-100% ethanol, respectively collecting all eluates, and concentrating to obtain a 90-100% ethanol elution part; 2, sequentially carrying out silica gel column chromatography, ODS column chromatography and semi-preparative liquid chromatography separation on the 90-100% ethanol elution part to obtain the compound. The compound can be used to prevent influenza A virus H1N1 or H3N2. The new lignanoid compound is extracted from the finished Reduning injection product, and the compound has a substantial antiviral effect; and the preparation method of the lignanoid compound has the advantages of simplicity in operation, strong controllability and good stability.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a novel compound and its preparation method and application. Background technique [0002] Reduning Injection (Guoyao Z20050217) is a second-class new drug of traditional Chinese medicine independently developed by Jiangsu Kangyuan Pharmaceutical Co., Ltd. It is a compound injection of traditional Chinese medicine. It is mainly used to treat colds, coughs, upper respiratory tract infections, and acute bronchitis caused by exogenous wind-heat clinically. Its clinical curative effect is definite and the effect is remarkable. [0003] In the early stage, in-depth research on the chemical components in Reduning Injection has been carried out, but the main components found are caffeoylquinic acid components and iridoid components, which have been confirmed by in vivo and in vitro experiments. The components have good antiviral effect, but the new compound disclosed in this patent an...

Claims

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Application Information

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IPC IPC(8): C07D307/00A61K31/343A61P31/12
CPCC07D307/00
Inventor 萧伟李海波姚新生于洋房卉李梦璇孟兆青黄文哲丁岗王振中胡晗绯
Owner JIANGSU KANION PHARMA CO LTD
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