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Two antitumor benzyl isoquinoline alkaloids containing chlorine substitutent in Thalictrum foliolosum

A technology of benzylisoquinoline and alkaloids, applied in the field of medicine

Inactive Publication Date: 2014-05-07
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The C-3 position of the isoquinoline structure involved in the present invention is replaced by a chlorine atom, and there is a new benzyl isoquinoline alkaloid compound substituted by a vinyl group on the benzyl fragment benzene ring, which has not been seen so far at home and abroad. Related patents or literature reports on similar compounds and activities

Method used

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  • Two antitumor benzyl isoquinoline alkaloids containing chlorine substitutent in Thalictrum foliolosum
  • Two antitumor benzyl isoquinoline alkaloids containing chlorine substitutent in Thalictrum foliolosum
  • Two antitumor benzyl isoquinoline alkaloids containing chlorine substitutent in Thalictrum foliolosum

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Take 15 kg of horsetail (Thalictrum foliolosum) medicinal material, extract twice with 75 L of ethanol with a volume fraction of 95% under reflux, and extract once with 75 L of ethanol with a volume fraction of 70% under reflux, and combine the 95% and 70% ethanol extractions After recovering under reduced pressure until there is no alcohol smell, use concentrated hydrochloric acid to adjust the pH value to 2-3, and the solution is separated by 001×7 type cation exchange resin column chromatography (resin volume is 3L), and eluted with distilled water until the eluent has no After coloring, it was eluted with 15L of 2% sodium hydroxide ethanol solution, the eluent was adjusted to pH 5.6 with concentrated hydrochloric acid and concentrated to 3L under reduced pressure, then extracted three times with equal volume of chloroform, and the obtained 36g extract was subjected to 200 -300 mesh basic Al 2 o 3 Column chromatographic separation, gradient elution with dichlorometh...

Embodiment 2

[0044] Example 2: In vitro growth inhibition experiments of the compound of formula I and the compound of formula II on human acute promyelocytic leukemia cell line HL-60 and human acute monocytic leukemia cell line U937:

[0045] HL-60 and U937 cell lines were cultured in 10% (V / V) heat-inactivated fetal bovine serum, 100IU / mL penicillin, 100μg / mL streptomycin and 0.2% NaHCO 3 RPMI-1640 medium, 37°C, 5% CO 2 Incubate in a saturated humidity incubator. Weigh trypan blue, add a small amount of distilled water to grind, add triple distilled water to dilute to 4%, filter with filter paper, and store at 4°C. When used, the stock solution was diluted to 0.4% working concentration with PBS. The monomer compound was prepared into a stock solution with a concentration of 100 mM in DMSO and stored at -20°C. When using, first dilute the mother solution in absolute ethanol, and directly add different volumes of alcohol solution into the culture plate to dilute to the required concentr...

Embodiment 3

[0047] MCF-7 and PC-3 cell lines were cultured in a medium containing 10% (V / V) heat-inactivated fetal bovine serum, 100IU / mL penicillin, 100μg / mL streptomycin and 0.2% NaHCO 3 RPMI-1640 medium, 37°C, 5% CO 2 Incubate in a saturated humidity incubator. Weigh MTT, add PBS to dissolve, prepare a 2mg / mL solution, stir in the dark for 30min, filter through a 0.22μm filter membrane, aliquot, and store at -20°C.

[0048] Take MCF-7 or PC-3 cells in the logarithmic growth phase, and use (2-3)×10 4 The density of cells / mL was inoculated in a 96-well culture plate, 100 μL in each well, and after 24 hours of making it adhere to the wall, 100 μL of the compound to be tested diluted to different concentrations with the culture medium was added, and the culture was continued at 37°C for 96 hours. 5-fluorouracil (5-FU) was used as a positive control. Then add 50 μL MTT solution to each well and incubate at 37°C for 4 hours, discard the supernatant, add 200 μL DMSO to each well, shake at ...

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Abstract

The invention belongs to the field of medicine technologies, and relates to two benzyl isoquinoline alkaloid compounds containing a chlorine substitutent, which have antitumor activity and are separated from Thalictrum foliolosum. The compounds provided by the invention are novel in structure, have remarkable in vitro antitumor activity for a human acute monocytic leukemia cell line U937, a human acute promyelocytic leukemia cell line HL-60, a human breast cancer cell line MCF-7 and a human prostate cancer cell line PC-3, and can be a lead compound used for developing a novel antitumor natural medicine.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to two kinds of benzylisoquinoline alkaloids containing chlorine atoms and having anti-tumor activity extracted and separated from the medicinal plant Ponytail of Ranunculaceae Tangsong and its preparation method . Background technique [0002] Alkaloids are the main chemical constituents of Thalictrum plants in the family Ranunculaceae. The alkaloids isolated from this genus have been reported so far: simple isoquinolines, benzyl isoquinolines , Apufei, protoberberine, morphinane, etc.; in addition, there are a large number of alkaloid dimers. [0003] There are more than 200 species of Echinacea in the world, and 67 species in my country, mainly concentrated in the southwest region. Among them, Thalictrum foliolosum DC. is a folk herbal medicine and Tibetan medicine that grows on the plateau at an altitude of 2300-3600 meters in Southwest China. Tang Yalin et al. reported (CN101...

Claims

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Application Information

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IPC IPC(8): C07D405/06A61K31/4725A61P35/00A61P35/02
CPCC07D405/06
Inventor 华会明苏钰清马冬珂李圣各李达翃李建勇郭佳
Owner SHENYANG PHARMA UNIVERSITY
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