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Juglone derivative and application thereof

A technology of juglone and derivatives, which is applied in the field of juglone and quinone compounds, can solve the problems that juglone has not yet been retrieved, and has not yet been retrieved, and achieve the effect of inhibiting tumor growth and metastasis, and inhibiting tumor angiogenesis

Inactive Publication Date: 2013-01-02
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

By consulting domestic and foreign research papers and patent documents, we have not yet retrieved reports that juglone (juglone) has the activity of inhibiting STAT3 signal transduction pathways, nor have we retrieved the new structure compound 2-ethoxy-6 specifically referred to in this patent. -Acetyl-7-methyljuglone and its derivative 2-methoxy-6-acetyl-7-methyljulquinone have related research literature reports on inhibiting STAT3 signal transduction pathway and anti-tumor activity

Method used

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  • Juglone derivative and application thereof
  • Juglone derivative and application thereof
  • Juglone derivative and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0064] 1. Separation of 2-ethoxy-6-acetyl-7-methyl-juglone

[0065] Take Polygonum cuspidatum root powder (400g), add petroleum ether (PE, 1000mL×3) ultrasonic extraction (40kHz, 45°C, 50% power, 30min), ultrasonic extraction solution was filtered with Buchner funnel to obtain filtrate, and the filtrate was obtained by rotating Evaporator concentrated and weighed to obtain the PE extract of Polygonum cuspidatum root (2.3g); the residue was added to EtOAc (1000mL×3), MeOH (1000mL×3), H 2 O (1000mL×2) was ultrasonically extracted sequentially, concentrated and dried to obtain the extract PE crude extract (2.3g), EtOAc crude extract (1.3g), MeOH crude extract (5.8g) and H 2 O crude extract (14.2g, four kinds of extracts of Polygonum cuspidatum root were used to test the activity of HepG2 cells stably transfected with STAT3 reporter. The test results showed that the inhibition rate of EtOAc crude extract on STAT3 regulation was 82.3 at 40 μg / mL. %. Use high performance liquid pha...

Embodiment 2

[0080] Polygonum cuspidatum rhizome coarse powder 9.5kg, added ethyl acetate (EtOAc) and extracted in Buchi automatic extractor under argon protection at 50°C (6L×4, 4x4min, 100pa), concentrated under reduced pressure to obtain Polygonum cuspidatum EtOAc (316g) extract . Take Polygonum cuspidatum EtOAc extract 15g, through silica gel column chromatography, use the mobile phase of petroleum ether-ethyl acetate with a volume ratio of 100:0, 98:2, 95:5, 90:10 and 80:20 to elute successively , collected the eluent of petroleum ether:ethyl acetate=98:2, and obtained 1.6g of chemical components; the chemical components (1.6g) were separated by Sephadex LH20 column, and the elution mobile phase was 100% ethanol, and the elution Liquid chromatography conditions are petroleum ether: ethyl acetate = 7:3 thin-layer chromatography, recover the eluent of thin-layer chromatography ultraviolet 356nm color red spots, concentrate under reduced pressure to obtain 0.34g of chemical microcomponen...

Embodiment 3

[0082] An appropriate amount of Polygonum cuspidatum sample was crushed and passed through a 24-mesh sieve. Using the yield of the extract as an indicator, multiple extraction condition parameters were compared to determine the supercritical CO 2 The optimal process conditions for extracting volatile components of pandanus powder are: extraction kettle pressure 15MPa, extraction temperature 45°C, desorption pressure 6.4MPa, desorption temperature 50°C, CO 2 The flow rate is 32L / h, the extraction time is 2h, and a small amount of ethanol is added as an entrainer. Get 2000g of Polygonum cuspidatum root powder and put it into the extraction kettle, heat the extraction kettle and the analysis kettle, cool the storage tank, when the temperature reaches the preset pressure, and adjust the CO 2 Flow rate, constant temperature and constant pressure circulation extraction, the extract was collected from the separation tank to obtain about 20mL of tan liquid, and the ethanol was removed...

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Abstract

The invention belongs to the field of organic chemistry, and in particular relates to a juglone derivative with a molecular structure shown as a formula (I). The juglone derivative stated in the invention has a chemical name 2-ethoxy-6-acetyl-7-methyl-juglone, a molecular formula of C15H14O5, and molecular weight of 274; and the juglone derivative is yellow needle crystal under normal temperature and pressure, and has a melting point of 153-154 DEG C. The compound stated in the invention can be separated from a traditional Chinese medicine Polygonum cuspidatum, has functions of inhibiting STAT3 (signal transducer and activator of transcription protein3) signal transduction pathway, and further inhibiting growth of tumor (stem) cells and inducing apoptosis of tumor cells, and can be used for preparing a STAT3 inhibitor and antitumor drugs.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to quinone compounds, in particular to juglone. Background technique [0002] STAT3 (signal transducer and activator of transcription3) is one of the important members of the signal transducer and activator of transcription family, and the STATs family includes STAT1, STAT2, STAT3, STAT4, STAT5a, STAT5b and STAT6 (Bowman, T., et al., 2000.Oncogene 19, 2474-2488.). STAT3 protein consists of about 770 amino acids, which can be divided into SH2 (Src-homology-2 domain) domain, DNA binding domain, supercoiled-coil domain, linker domain and amino terminal according to its function and structure domain. The STAT3 signaling pathway can be activated and phosphorylated by various cytokines such as IL-6, JAKs and EGFR, and transferred into the nucleus in the form of dimer activation (p-STAT3), acting on specific DNA fragments in the nucleus to regulate the transcription of target genes ( Bromb...

Claims

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Application Information

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IPC IPC(8): C07C50/38C07C46/10A61K31/122A61P35/00
Inventor 刘嘉炜俞强陈蔚文张卿陈考坛刘景丽李武国司马贞华匡珊
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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