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Compound separated out from labiatae isodon plant, and preparation method and application thereof

A technology of the genus and compound of Camellia genus, which is applied in the field of medicine, can solve problems such as unclear relationships, and achieve the effect of strong pharmacological effects and good medicinal prospects

Active Publication Date: 2017-05-10
JIANGSU PROVINCE INST OF TRADITIONAL CHINESE MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research on the chemical constituents of Isodon forrestii var. forrestiiIso A has not been reported in the literature, and the application of the active ingredients of this plant in the preparation of anti-tumor drugs, especially the relationship with the thioredoxin signaling pathway is not clear

Method used

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  • Compound separated out from labiatae isodon plant, and preparation method and application thereof
  • Compound separated out from labiatae isodon plant, and preparation method and application thereof
  • Compound separated out from labiatae isodon plant, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation method of embodiment 1 compound Iso A

[0043] Take 10Kg of the aerial part of the plant Isodon forrestii var.forrestii and pulverize it, soak it with 70% (acetone: water) acetone water at room temperature for three times, a total of 12 liters, evaporate the acetone by distillation under reduced pressure, and extract the remaining part with ethyl acetate to obtain ethyl acetate The extract was subjected to silica gel column chromatography, 200 mesh pore size silica gel, chloroform: acetone (volume ratio 1:0.11) solvent washing, and repeated treatment with a mixed solution of 85% ethyl methanol and water through RP-18 volume ratio, and finally obtained Iso A500mg , The yield is about 0.005%.

[0044] X-single crystal of compound Iso A and physical and chemical data such as UV, optical rotation, infrared, NMR:

[0045] Crystal data for Sze1:C 28 h 38 o 10 , M=534.58, orthorhombic, α=90.00°, β=90.00°, γ=90.00°, T=100(2)K, space group P212121, Z=4,...

Embodiment 2

[0047] The preparation method of embodiment 2 compound Iso A

[0048] Take 10Kg of the aerial part of the plant Isodon forrestii var.forrestii and pulverize it, soak it three times with 80% (acetone: water) acetone water at room temperature, a total of 20 liters, evaporate the acetone by distillation under reduced pressure, and extract the remaining part with ethyl acetate to obtain ethyl acetate The extract was subjected to silica gel column chromatography, 300 mesh pore size silica gel, chloroform: acetone (1:0.5) solvent washing, and repeated treatment with RP-18 and a mixed solution of 85% acetonitrile and water by volume to finally obtain Iso A 400mg, The yield is about 0.004%.

Embodiment 3

[0049] Example 3 Iso A can selectively inhibit the growth of human tumor cells and induce apoptosis

[0050] Iso A (purity>99%) was dissolved in DMSO, the stock solution concentration was 40mM, and stored at -20°C. Using MTT method to detect IsoA in a variety of tumor cells, including liver cancer, breast cancer, lung cancer, osteosarcoma, melanoma, cervical cancer, etc., as well as normal cells human liver cell LO2, human embryonic lung cell HFL1, human breast epithelial cell MCF 10A Inhibitory effect. Compared with normal cells, Iso A has a stronger inhibitory effect on tumor cells, and its IC50 values ​​are all less than 30 μM ( figure 2 ). Among the tested cells, HepG2 cells are the most sensitive to Iso A, so HepG2 was chosen as the model for subsequent experiments. MTT assay showed that Iso A could inhibit the growth of HepG2 cells in a concentration-dependent manner, but had no significant inhibitory effect on LO2 cells ( image 3 ). Further trypan blue experiment...

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Abstract

The invention discloses a compound having a structure shown in Formula I or a pharmaceutically acceptable salt thereof, and a preparation method and application thereof. The compound having the structure shown in Formula I is structurally novel and has not been reported in documents, is separated out form a labiatae isodon plant, and can be used as a compound for Trx1 selective depressant. The invention also discloses a pharmaceutical composition and preparation of the compound having the structure shown in Formula I, and application thereof in preparation of medicines for preventing or treating cancer. The Iso A disclosed by the invention is safe, low in toxicity and strong in pharmacological action, and shows excellent pharmaceutical prospects.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a compound isolated from a plant belonging to the family Lamiaceae, and a preparation method and application thereof. Background technique [0002] The thioredoxin system includes thioredoxin (Trx), thioredoxin reductase (TrxR) and nicotinamide adenine dinucleotide (NADPH), and is a widely distributed NADPH-dependent Disulfide reductase system. Trx has two isoforms, Trx1 and Trx2, which have similar functions but have different localizations in cells. Trx1 is located in the cytoplasm, nucleus and extracellular matrix, and Trx2 is mainly located in the mitochondria. Trx1 is a protein composed of 104 amino acids, and its active site is composed of cysteine-glycine-proline-cysteine ​​(-Cys-Gly-Pro-Cys-) conserved form. The reduction mechanism of Trx is that after it binds to the substrate X-S2, in the hydrophobic environment of the complex, the sulfhydryl group of Cys32 acts a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/21C07C67/48A61K31/22A61P35/00
CPCC07C67/48C07C69/21A61K36/00C07C2603/86A61K36/53A61K2236/00A61P35/00C07C69/12
Inventor 曹鹏普建新孙晓艳孙汉董汪伟光陈姣蔡雪婷杜雪
Owner JIANGSU PROVINCE INST OF TRADITIONAL CHINESE MEDICINE
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