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Beta-carboline alkaloid and application thereof to preparing antimalarial medicaments

An alkaloid, anti-malarial technology, applied in the direction of anti-infective drugs, drug combinations, resistance to vector-borne diseases, etc., can solve problems such as failure and reduction of drug efficacy

Inactive Publication Date: 2011-11-23
SOUTH CHINA SEA INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problem facing malaria treatment at present is that the drug resistance of Plasmodium leads to the reduction or even failure of drug efficacy

Method used

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  • Beta-carboline alkaloid and application thereof to preparing antimalarial medicaments
  • Beta-carboline alkaloid and application thereof to preparing antimalarial medicaments
  • Beta-carboline alkaloid and application thereof to preparing antimalarial medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the preparation of the β-carboline alkaloid shown in formula (I):

[0019] 1. Seed culture:

[0020] (1) Preparation of seed medium: Weigh 40g of glucose, 4g of peptone, 4g of yeast extract, and 5g of sea salt, dissolve them in 2000mL of tap water, distribute them in eight 500mL Erlenmeyer flasks, and sterilize at 121°C for 25 minutes to obtain Sterilized seed medium.

[0021] (2) Cultivation of seeds: Insert the bacterial strain of marine actinomycetes (M.thermotolerans) SCSIO 00652 into the above-mentioned seed culture medium, and at a temperature of 28° C., place on a shaker at a speed of 150 rpm and cultivate for 60 hours to obtain seeds culture medium.

[0022] 2. Fermentation culture:

[0023] (1) Preparation of fermentation medium: take 100 g of soluble starch, K 2 HPO 4 10g, MgSO 4 .7H 2 O 10g, (NH 4 ) 2 SO 4 20g, CaCO 3 20g, FeSO 4 .7H 2 O 0.01g, MnCl 2 .7H 2 O 0.01g, 30g of coarse sea salt, dissolved in 10000mL of water, adjusted...

Embodiment 2

[0029] The compound isolated in Example 1 was subjected to structural analysis and testing to obtain the following physical and chemical property data:

[0030] β-carboline alkaloid 1: Pale yellow needle-like crystals; UV(PDA)λ max 220, 285, 374nm; NMR data are shown in Table 1;

[0031] (-)-ESI-MS m / z 386[M-H] - ;(-)-HR-ESI-MS m / z 386.1519[M-H] - (C 23 h 20 N 3 o 3 , theoretical value 386.1505).

[0032] β-carboline alkaloid 2: Pale yellow solid; UV(PDA)λ max 221, 285, 374nm; NMR data are shown in Table 1;

[0033] (-)-ESI-MS m / z 372[M-H] - ;(-)-HR-ESI-MS m / z 372.1350[M-H] - (C 22 h 19 N 3 o 3 , theoretical value 372.1354).

[0034] β-carboline alkaloid 3: Pale yellow solid; UV(PDA)λ max 218, 282, 373nm; NMR data are shown in Table 1;

[0035] (-)-ESI-MS m / z 356[M-H] - ;(-)-HR-ESI-MS m / z 356.1421[M-H] - (C 22 h 19 N 3 o 2 , theoretical value 356.1404).

[0036] β-carboline alkaloid 4: Pale yellow solid; UV(PDA)λ max 219, 282, 375nm; NMR data are shown...

Embodiment 3

[0054] The compounds separated and purified in Example 1: β-carboline alkaloid 1, β-carboline alkaloid 2, β-carboline alkaloid 3 and β-carboline alkaloid 4 were tested to inhibit the growth of Plasmodium.

[0055] The specific steps are as follows: culturing human Plasmodium falciparum drug-sensitive strain 3D7 and multi-drug-resistant strain Dd2 in vitro with RMPI 1640 medium and human AB serum with a volume fraction of 10%, and the hematocrit is about 2%. Plate cultured Plasmodium parasites at an initial infection rate of 0.2%, 90 μL per well. Dissolve the compound to be tested in DMSO to make a mother solution, and then dilute it with the medium. When the activity is detected, the concentration gradient is 2-fold gradient dilution, and the drug solution accounts for 10% of the volume fraction of the culture system (the concentration of DMSO is less than 0.5% of the volume fraction) , which is 10 μL. at 37°C, CO 2 Cultured in the incubator for 72h. Then add 100 μL of lysi...

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Abstract

The invention discloses a beta-carboline alkaloid and application thereof to preparing antimalarial medicaments. The structure of the beta-carboline alkaloid is as shown in a formula (I) described in the specification. The beta-carboline alkaloid disclosed by the invention or pharmaceutical salt thereof plays a killing role on plasmodia, can be used for preparing the antimalarial medicaments and treating plasmodium infectious diseases and provides more drug choices for treating malaria. R is expressed in the formula (I), wherein R1=OMe, OH or H.

Description

Technical field: [0001] The invention relates to a class of beta-carboline alkaloids and their application in the preparation of antimalarial drugs. Background technique: [0002] Malaria (malaria), commonly known as "beating the pendulum", is an insect-borne parasitic disease transmitted by Plasmodium through mosquito bites. Clinically, the main features are periodic attacks of chills, high fever, headache, sweating, anemia and splenomegaly. Due to differences in protozoan strains, degree of infection, immune status, and body reactivity, it can be divided into Plasmodium vivax, Plasmodium vivax, Plasmodium falciparum, and Plasmodium ovale according to clinical symptoms and attack patterns. The incidence rate of children is high, and it can fall ill all year round in tropical and subtropical regions, and is widely prevalent in all parts of the world. According to the statistics of the World Health Organization, 92 countries and regions are still highly and moderately endem...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/437A61P33/06
CPCY02A50/30
Inventor 鞠建华黄洪波姚月良田新朋张长生
Owner SOUTH CHINA SEA INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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