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Cardiac glycoside compounds and antitumor application thereof

A compound, cardiac glycoside technology, applied in the field of medicine, can solve problems such as less toxic anticancer drugs

Inactive Publication Date: 2011-10-19
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, although a lot of research has been done on anticancer drugs, such as cisplatin, vinblastine, camptothecin, and its derivatives, paclitaxel and other anticancer active drugs have been discovered, but there is no good activity and little or no toxicity. The emergence of broad-spectrum or narrow-spectrum anticancer drugs

Method used

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  • Cardiac glycoside compounds and antitumor application thereof
  • Cardiac glycoside compounds and antitumor application thereof
  • Cardiac glycoside compounds and antitumor application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: dark elimination vine ( Streptocaulon juventas ) Extraction and separation of cardiac glycosides:

[0039] dark wilting vine ( Streptocaulon juventas ) roots (10kg) were extracted twice with 60% ethanol under reflux, each time for 1.5h, the extracts were combined, and the ethanol was recovered under reduced pressure until there was no alcohol smell. Disperse the ethanol extract in water to form a suspension, adjust the density to 1.07, load the sample on the macroporous adsorption resin (HPD100) column chromatography, elute with 20% ethanol, 55% ethanol, and 90% ethanol successively, and collect 55% ethanol The eluate was concentrated to obtain a fraction eluted with 55% ethanol (145 g). The eluted part was separated by silica gel column chromatography, eluted with dichloromethane: methanol system, and divided into 5 fractions A-E, of which fraction B (9.5g) was passed through a silica gel column (dichloromethane: methanol 15:1), reverse phase Compoun...

Embodiment 2

[0040] Embodiment 2: Malian saddle ( Streptocaulon griffithii ) Extraction and separation of cardiac glycosides:

[0041] Ma Lian saddle ( Streptocaulon griffithii ) roots (10kg) were extracted twice with 60% ethanol under reflux for 1.5 hours each time, the extracts were combined, concentrated, and dried to obtain the extract. The extract was dissolved in water, extracted three times with an equal volume of dichloromethane, then extracted three times with n-butanol, collected the n-butanol extract, and concentrated to obtain the n-butanol layer extract (92 g). The extract was divided into 5 fractions H-L through a silica gel column (ethyl acetate-methanol), fraction I (10g) was passed through a silica gel column (dichloromethane:methanol 15:1), reversed-phase silica gel column (50% methanol-water ) and recrystallization to obtain compound 1 and sub-fraction I1. I1 was purified by preparative HPLC with 55% methanol as the mobile phase to obtain compounds 9 and 12. Fracti...

Embodiment 3

[0043] Embodiment 3: in embodiment 1 and embodiment 2, have the in vitro tumor inhibition experiment of the cardiac glycoside compound of general formula (I):

[0044] Cardiac glycoside compounds 1-13, compounds 7 and 11 compositions, and compound 1-13 mixed in equal proportions were tested by MTT method on Hela cervical cancer cells, HT29 human colon cancer cells, and A549 human lung adenocarcinoma cells. , SUP-B15 acute lymphoblastic leukemia cells, SGC7901 human gastric cancer cells, and Huh-7 human liver cancer cells in vitro tumor inhibitory activity (results are shown in Table 5). The activity test method is as follows:

[0045] The experiment set up a negative control group (water), a DMSO solvent control group, a positive control group (paclitaxel) and 5 different concentrations (0.01, 0.1, 1, 5, 1 0μm) of samples to be tested (compounds 1~13, 7 and 11 composition, a composition mixed in equal proportions of 1 to 13). Hela, HT29, A549, SUP-B15, SGC7901, and Huh-7 tum...

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Abstract

The invention belongs to the technical field of medicaments and in particular relates to cardiac glycoside compounds with a general formula (I), as well as derivatives, stereoisomers, a racemic mixture or a non-racemic mixture of the stereoisomers and pharmaceutically acceptable acid addition salts or solvates, wherein R1 is CH3, CHO or CH2OH; R2 is H or a linear saccharide chain or a branched saccharide chain, the linear saccharide chain or the branched saccharide chain is formed by saccharides; and these acids comprise inorganic acids like hydrochloric acid, sulfuric acid, hydrobromic acid, phosphoric acid, nitric acid, carbonic acid and the like as well as organic acids like methanoic acid, acetic acid, succinic acid, citric acid, lactic acid, fumaric acid, tartaric acid, benzoic acid, p-methyl-benzenesulfonic acid, methylsulphonic acid, naphthalenesulfonic acid, gluconic acid and the like. The cardiac glycoside compounds can be obtained by separation from plants, in particular Streptocaulon plant juventas or Streptocaulon griffithii, by using multiple conventional separating means or obtained through synthesis, semisynthesis or bioconversion means. These compounds have excellent inhibiting and treatment effects on multiple tumor cells.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a class of cardiac glycoside compounds and their antitumor application. Background technique [0002] Cancer is mainly caused by chemical, physical and biological (mycotoxins, viruses, etc.) carcinogens. Although a lot of research has been done on anticancer drugs, such as cisplatin, vinblastine, camptothecin, and its derivatives, paclitaxel and a series of anticancer active drugs have been found, but there is no good activity and little or no toxicity. The emergence of broad-spectrum or narrow-spectrum anticancer drugs. Therefore, the development and exploration of a broad-spectrum and narrow-spectrum anticancer active compound with high efficiency, low toxicity, and dual efficacy of treatment and prevention has become a research work of great significance. [0003] Asclepiadaceae (Asclepiadaceae) Ma Lian ( Streptocaulon ) There are 5 species of plants distributed in India, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J19/00A61K31/7048A61K31/585A61P35/00
CPCA61P35/00A61P35/04C07J19/00C07J19/005
Inventor 殷军韩娜薛睿夏明钰杨静玉
Owner SHENYANG PHARMA UNIVERSITY
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