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New compound and preparation method thereof

A compound, the technology of n-hexane, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problem of difficult to ensure the effectiveness of clinical medication, safety and sustainability, lack of material basis for drug effect and drug effect research, zedoary volatile oil Complicated components and other issues, to achieve quality and controllable drug use, broaden the source of raw materials, good separation effect

Active Publication Date: 2016-05-25
TIANJIN YAOYU BIOLOGICAL TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the application of traditional Chinese medicine Curcuma is mainly based on its volatile oil injection and compound Curcuma oil for anti-cancer effect, which is relatively limited.
In addition, the components of zedoary volatile oil are complex, and the anticancer effects of different components are also very different. The lack of necessary material basis and efficacy research, and the lack of reasonable quality control standards make it difficult to ensure the effectiveness, safety and reliability of clinical medication. Persistent

Method used

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  • New compound and preparation method thereof
  • New compound and preparation method thereof
  • New compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Use curcuma as raw material, grind it into powder, weigh 4kg, dissolve it in 25L of 98% ethanol solution, and carry out reflux extraction, and finally obtain the filtrate by rotary evaporation to dryness, and then dissolve it in n-hexane-ethanol with a volume fraction of n-hexane of 70%. In a binary mixed solvent, prepare an extract with a concentration of 100 mg / mL, pass through a 0.45 μm microporous membrane, and prepare by one-dimensional liquid chromatography.

[0042] One-dimensional liquid chromatography adopts Silica150×250mm, 10μm, The mobile phase adopts the mixture of organic phases, wherein the organic phase A phase is n-hexane, B phase is ethanol, gradient elution mode: B phase concentration 0-50% gradient elution for 30 minutes. Adopt the ultraviolet detector 210nm to select the absorption wavelength, the preparation temperature is room temperature, the injection volume is 100mL / needle, the mobile phase flow rate is 600mL / min, collect the component of 15.5...

Embodiment 2

[0046] The purpose component that embodiment 1 obtains utilizes analytical chromatographic column to carry out purity test, as image 3 As shown, the purity reaches 99%, and it is a monomeric compound. The chromatographic column selects the normal phase silica gel chromatographic column Silica4.6×250mm, 10μm,

[0047] The target monomer compound was subjected to NMR analysis (BrukerA.GAVIII600PLUS, Hanmeng Biotechnology (Tianjin) Co., Ltd.), and the NMR spectrum was as follows: Figure 4 , 5 As shown, the NMR data of the monomer compound obtained according to 1HNMR and 13CNMR spectrograms are shown in Table 1.

[0048] Table 1: 1HNMR (600MHz) and 13CNMR (600MHz) (CDCl 3 ,TMS,ppm)

[0049] Carbon number

δC

δH(JinHz)

1

134.05

4.90(d,10.4)

2

27.30

1.95(m)2.26(m)

3

36.13

1.71(m)2.05(m)

4

47.91

2,47(m)

5

209.27

6

40.26

3.30(d,15.2),3.58(d15.2)

7

154.45

...

Embodiment 3

[0053] Embodiment 3: Human liver cancer cell Hep--G2 experiment

[0054] Combine the eight-well plate (E-PlateL8) produced by Eisen Bio (Hangzhou) Co., Ltd. with the iCELLigence real-time label-free cell function analyzer, add 150ulF-12K medium to each well, and place at 37°C, 5% CO 2 In the incubator, adjust the background data to between 40-130. The compound sample (EZ-8-3) isolated in Example 1 was completely dissolved to 50 mg / ml with dimethyl sulfoxide, and then diluted into a 5 mg / ml working solution with F-12K medium, and the cultured Human liver cancer cells Hep-G2 were digested with trypsin and diluted to 4×10 4 / ml live cell suspension, inoculated in eight-well plate, 345ul per hole, added 5ul of working solution to make the final concentration 50μg / ml, and added 5ul of 1‰ dimethyl sulfoxide F- 12K medium, placed at 37°C, 5% CO 2 culture medium for 72 hours. The results showed that the target monomer compound 8-hydroxy-jima-1,7-dien-5-one-8,12-lactone significant...

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Abstract

The invention provides a new compound, which has a molecular formula of C15H20O3, a molecular weight of 248, and a Chinese name of 8-hydroxy-Germa-1, 7-diene-5one-8, 12-lactone. The preparation method includes: taking curcuma zedoaria tuber as the raw material, conducting grinding into powder, then performing ethanol extraction, concentrating the filtrate, then dissolving the product in a n-hexane-ethanol mixed solvent; conducting one-dimensional liquid chromatography separation: employing a normal phase silica gel chromatographic column, adopting a binary mobile phase with n-hexane as the phase A and ethanol as the phase B, carrying out elution with the phase B at a concentration of 0-50%, and collecting the 15.5-17min eluent; performing dissolving with the n-hexane-ethanol mixed solvent; conducting two-dimensional liquid chromatography separation: employing an Acchrom X-Amide chromatographic column, adopting a binary mobile phase with n-hexane as the phase A and ethanol as the phase B, carrying out elution with the phase B at a concentration of 0-30%, and collecting the 17-18min eluent so as to obtain a target product. The new compound is proved to have anti-liver cancer and anti-lung cancer biological activity and can be used for preparation of related drugs.

Description

technical field [0001] The invention relates to the technical field of traditional Chinese medicine products, in particular to a novel compound extracted from the traditional Chinese medicine zedoary tuber. Background technique [0002] The traditional Chinese medicine Zedoary is the rhizome of the turmeric plant in the ginger family. Zedoary has the effects of promoting qi, breaking blood, eliminating stagnation and relieving pain. Modern pharmacological studies have shown that zedoary volatile oil has anti-tumor and antibacterial effects; curcumol has anti-tumor effects and anti-early pregnancy effects. In addition, curcuma has significant effects on cardiovascular, gastrointestinal smooth muscle, and acute renal failure, and also has hepatoprotective effect. [0003] At present, the application of traditional Chinese medicine Curcuma is mainly based on its volatile oil injection and compound Curcuma oil for anticancer effect, and it is relatively limited to make anticanc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93A61P35/00
CPCC07D307/93
Inventor 张耀洲韩朝盖其静杜思邈
Owner TIANJIN YAOYU BIOLOGICAL TECH
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