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Preparation method for novel cepharanthine and application of cepharanthine in pharmaceuticals

A technology of Stephalin and its chemical structural formula, which is applied in the preparation of new Stephalin and its application in medicine

Inactive Publication Date: 2016-11-30
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

We extracted a new type of patinol from the roots of Rhizoma chinensis, and its structure is (1R, 1′R)-paternil, which has not been reported in the literature

Method used

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  • Preparation method for novel cepharanthine and application of cepharanthine in pharmaceuticals
  • Preparation method for novel cepharanthine and application of cepharanthine in pharmaceuticals
  • Preparation method for novel cepharanthine and application of cepharanthine in pharmaceuticals

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Extraction and preparation of (1R, 1′R)-stephalin:

[0019] Purchase 5 kg of root tubers from Anguo Traditional Chinese Medicine Market, crush them, extract 3 times with an appropriate amount of 80% alcohol, concentrate under reduced pressure at 45°C to obtain 80 g of extracted crude extract, dissolve the crude extract in water, and extract 5 times with appropriate amount of ethyl acetate , to obtain extract 50g. The extract was mixed with 200-300 mesh silica gel, then eluted with petroleum ether / ethyl acetate (4:1, 3:2, 2:3, 1:4, pure ethyl acetate) to obtain Fr.1 - 5 components, component Fr.3 was repeatedly separated by silica gel chromatography column, Sephadex LH-20 gel chromatography column, and RP-C18 reverse-phase packing chromatography column to obtain 10 mg of the target compound.

Embodiment 2

[0021] Identification of (1R, 1′R)-stephalin structure:

[0022] Qualitative analysis data and collection of illustrative plates of the compound prepared in embodiment 1:

[0023] 1 H NMR (600MHz, CDCl 3 )δ: 2.38-2.44, 2.63-2.68 (2m, 2×2H, 2×NCH 2 ), 2.56(s, 3H, N-Me), 2.64(s, 3H, N-Me), 2.76-2.79, 2.84-2.87(m, 2×2H, 2×CH 2 ), 3.60(s, 1H, CH), 3.68(s, 3H, OMe), 2.98-3.31(m, 4H, 2×CH 2 ), 3.88(s, 3H, OMe), 4.17(s, 1H, CH), 5.59, 5.55(ds, 2H, OCH 2 O), 5.47(s, 1H, C 6 h 3 ), 6.32(s, 1H, C 6 h 2 ), 6.64(s, 1H, C 6 h 2 ), 6.77 (ds, 2H, C 6 h 3 ), 6.35(s, 1H, C 6 h 1 ), 7.03(s, 1H, C 6 h 4 ), 6.36(s, 1H, C 6 h 4 ), 6.95(s, 1H, C 6 h 4 ), 7.37 (d, J=7.9Hz, 1H, C 6 h 4 );

[0024] 13 C NMR (150MHz, CDCl 3 )δ: 25.8(C-4'), 28.9(C-4), 37.9(C-a), 40.3(C-a'), 42.3(N-Me), 43.9(N-Me), 45.3(C-3') , 51.2(C-3), 55.0(OMe), 56.0(OMe), 61.9(C-1'), 64.2(C-1), 100.4(O-CH 2 -O), 102.2(C-5′), 110.9(C-13), 111.1(C-5), 116.8(C-10), 118.5(C-8), 120.9(C-11′), 122.2( C-13'), 12...

Embodiment 3

[0040] Determination of Antitumor Activity of (1R,1′R)-Stephalin

[0041] 1. Principle of antitumor activity

[0042] MTT method is a method to detect cell survival and growth. Based on the living cell metabolite reducing agent thiazolyl blue [3-(4,5-dimethyl-2-thiazole)-2,5-diphenyltetrazolium bromide, MTT]. MTT is a dye that accepts hydrogen atoms. The NADP-related dehydrogenase in the mitochondria of living cells can convert yellow MTT into insoluble blue-purple formazon (formazon), while dead cells have no such function. After dissolving formazon with DMSO, measure the optical density value with a microplate reader at a certain wavelength, which can quantitatively measure the survival rate of cells. The inhibitory effect of the sample on the tumor cells was observed according to the change of the optical density value.

[0043] 2. Antitumor activity experiment

[0044] Cell lines: human cervical cancer cells (Hela), human lung cancer cells (A549), human breast cancer ...

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Abstract

The invention relates to (1R,1'R)-cepharanthine represented by a chemical structural formula 1 shown in the description, a preparation method therefor and use of the (1R,1'R)-cepharanthine. The (1R,1'R)-cepharanthine is extracted from Epigeal Srephaia tubers. The (1R,1'R)-cepharanthine has good inhibiting activity to human cervical carcinoma cells (Hela), human lung cancer cells (A549) and human mammary cancer cells (MCF-7) and can be used for preparing antitumor drugs. A third aspect of the technical scheme of the invention is to provide an application of the (1R,1'R)-cepharanthine described in a first aspect in the preparation of the antitumor drugs.

Description

technical field [0001] The present invention relates to the preparation and application of a class of novel compounds, in particular stepegrin and its application in the preparation of antitumor drugs. Background technique [0002] In 1938, Kondoh and Keimatsu determined for the first time that the structure of cepharanthine was (1R, 1′S)-cepharanthine. The bisbenzylquinoline alkaloids are the main components of Cepharanthine in the genus Cepharanthine. It has anti-tumor, immune regulation and antibacterial effects, and is used for agranulocytosis caused by radiotherapy and chemotherapy or leukopenia caused by other reasons [Moshe Rogosnitzky et al., Pharmacological Reports, 2011, 63, 337-347]. We extracted a new type of stepherin from the roots of Rhizoma chinensis, and its structure is (1R, 1′R)-stepherin, which has not been reported in the literature. [0003] (+)-Cepharanthine (Cepharanthine) molecular formula is C 37 h 38 N 2 o 6 , the molecular weight is 606.71, a...

Claims

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Application Information

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IPC IPC(8): C07D491/22A61P35/00
CPCC07B2200/07C07D491/22
Inventor 朱华结赵丹曹飞李婉
Owner HEBEI UNIVERSITY
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