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Dearylated isopentenyl acylated phloroglucinol meroterpenoid compound as well as pharmaceutical composition and application thereof

A technique for aromatizing isopentenyl acylated phloroglucinol and acyl phloroglucinol, which is applied in the application of arrhythmia and heart failure drugs, angina pectoris, and the field of myocardial ischemia treatment, which can solve the problem of poor selectivity and drug efficacy Insufficient, side effects and other problems, to achieve the effect of convenient operation

Active Publication Date: 2020-06-05
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, almost all of these molecules have problems such as poor selectivity, insufficient drug efficacy, and large side effects. There is still an urgent need for new late sodium current inhibitory active molecules in the market.

Method used

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  • Dearylated isopentenyl acylated phloroglucinol meroterpenoid compound as well as pharmaceutical composition and application thereof
  • Dearylated isopentenyl acylated phloroglucinol meroterpenoid compound as well as pharmaceutical composition and application thereof
  • Dearylated isopentenyl acylated phloroglucinol meroterpenoid compound as well as pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0033] The present invention provides the preparation method of compound hypulatone A and hypulatone B described in the above technical scheme, comprising the following steps: extracting the whole herb (12kg) of dried Rhizoma chinensis (12kg) with methanol for 3 times, each time for 2 days, and the obtained extract is reduced Press distillation to obtain the extract, mix the extract with 100-200 mesh silica gel, carry out silica gel column chromatography, the eluent used is chloroform, and obtain the chloroform section, and then mix the obtained chloroform section with polyamide to obtain 70%–100% methanol–water was used as the mobile phase to pass through the MCI column, and five components A to E were collected sequentially. The A (16.4g) component was subjected to silica gel column chromatography under gradient elution conditions, and petroleum ether / Acetone was used as the eluent to collect 5 fractions sequentially, which were recorded as fractions A1-A5; fraction A2 was s...

Embodiment 1

[0043] The preparation method of compound hypulatone A and hypulatone B comprises the following steps:

[0044] The present invention provides the preparation method of compound hypulatone A and hypulatone B described in the above technical scheme, comprising the following steps: extracting the whole herb (12kg) of dried Rhizoma chinensis (12kg) with methanol for 3 times, each time for 2 days, and the obtained extract is reduced Press distillation to obtain the extract, mix the extract with 100-200 mesh silica gel, carry out silica gel column chromatography, the eluent used is chloroform, and obtain the chloroform section, and then mix the obtained chloroform section with polyamide to obtain 70%–100% methanol–water was used as the mobile phase to pass through the MCI column, and five components A to E were collected sequentially. The A (16.4g) component was subjected to silica gel column chromatography under gradient elution conditions, and petroleum ether / Acetone was used as...

Embodiment 2

[0059] The dearomatization isopentenyl acylated phloroglucinol derivatives hypulatone A and hypulatone B of the present invention are to Na v 1.5 Late sodium current inhibitory activity test methods and results are as follows:

[0060] 1. Cell preparation and expression

[0061] Human embryonic kidney (HEK) 293 cells were cultured in DMEM (HyClone) medium supplemented with 10% calf serum (Gibco) and double antibodies of penicillin (100 units / ml) and streptomycin (0.1 mg / ml) (Biological Industries) . 293 cells in the logarithmic growth phase were treated with LipoD293 TM (SignaGen Laboratories) transfection reagent human pCDNA3.1-Na v 1.5, pCDNA3.1-hERG, pCDNA3.1-K v 1.5, pCDNA3.1-Ca v 3.1 and pCDNA3.1-EGFP plasmids were transfected into cells. Transfected human embryonic kidney (HEK) 293 cells should be used within 48 hours.

[0062] 2. Electrophysiology experiment

[0063] All experiments were performed at room temperature (22-25°C). Using a microelectrode puller (P-10...

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Abstract

The invention provides a preparation method of dearylated isopentenyl acylated phloroglucinol meroterpenoid hypulatone A and hypulatone B. The preparation method comprises the following steps: preparing dearylated isopentenyl acylated phloroglucinol meroterpenoid A and hypulatone B; the invention also discloses a preparation method of the compound, a pharmaceutical composition taking the compoundas an active ingredient, and application of the compound in medicines, especially medicines for treating myocardial ischemia, angina pectoris, arrhythmia, heart failure and other diseases. The new compounds Hypulatone A and Hypulatone B provided by the invention are meroterpenoid compounds of sesquiterpene with a complex structure and dearylated isopentenyl acylated phloroglucinol. The structuralformula of the new compounds is shown in the specification. Hypulatone A and Hypulatone B have the activity of selectively and remarkably inhibiting late sodium current; the compound Hypulatone B is anatural inhibitor with the strongest activity at present, the effect of Hypulatone B is 30 times that of positive control ranolazine, and the compound Hypulatone B has obvious advantages and potential medicinal value. The compound can be used for preparing medicines for preventing and / or treating heart system diseases.

Description

technical field [0001] The present invention relates to the field of pharmaceutical technology, in particular to v 1.5 Hypulatone A and hypulatone B, novel compounds with sodium ion channel inhibitory activity, their preparation methods, and their application in the treatment of myocardial ischemia, angina pectoris, arrhythmia, and heart failure. Background technique [0002] Hypericum (Hypericum) is a large genus in the family Guttiferae, with about 400 species worldwide. There are about 55 species and 8 subspecies in my country, which are distributed all over the country, and are mainly produced in the southwest region. The plants of this genus are widely used as medicinal plants at home and abroad, and have a long history. For example, there are 25 species of Hypericum plants in my country that are used as medicines among the people, and have various pharmacological activities such as antidepressant, antitumor, antiviral and antibacterial. So far, various types of acti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10A61K31/343A61P9/10A61P9/06
CPCC07D493/10A61P9/10A61P9/06
Inventor 许刚年寅叶岩松杜叔宗姜娜娜
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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