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Biflavonoid compound as well as preparation method and application thereof

A technology of double flavonoids and compounds, applied in the field of medicinal chemistry, can solve problems such as prolonging the survival period of patients, and achieve the effects of significant curative effect, moderate effective dose and small side effects

Active Publication Date: 2019-06-11
SHENZHEN PEOPLES HOSPITAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, the use of Sorafenib only prolongs the patient's survival by three months

Method used

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  • Biflavonoid compound as well as preparation method and application thereof
  • Biflavonoid compound as well as preparation method and application thereof
  • Biflavonoid compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The characterization of embodiment 1 (5,7,8,4'-tetrahydroxyflavone)-3'-4-(5,7-dihydroxyflavone)

[0039] The new biflavonoid compound provided by the present invention is a yellow needle-like crystal, and ESI-MS (Positive) gives a quasi-molecular ion peak m / z561[M+Na] + , and HR-ESI MS (Negative) gives a quasi-molecular ion peak m / z 537.0628[M-H] - , suggesting that its molecular weight is 538; 1 H and 13 C NMR confirmed its molecular formula as C 30 h 18 o 10 , with a calculated unsaturation of 22.

[0040] see Figure 1-7 , the hydrogen spectrum and carbon spectrum of the biflavonoids suggest that it contains two hydroxyl groups, one five-membered A ring, one four-membered A' ring, one 1,3,4-trisubstituted B ring and 1 , 4-disubstituted B'ring. Consider the A and B rings as whole I, and the A' and B' rings as whole II. In NOESY spectrum, compound H-3 of the present invention (δ H 6.85) related to H-2' and 6' and H-3' (δ H 6.81) is related to H-2" and 6", a...

Embodiment 2

[0044] Example 2 Extracting (5,7,8,4'-tetrahydroxyflavone)-3'-4-(5,7-dihydroxyflavone) from Flos Lonicerae

[0045] At room temperature, 6.5 kg of honeysuckle (dried) were cold soaked and percolated for 3 times with 75% ethanol, and the extracts were combined. Then, the solvent was recovered under reduced pressure at 55 ° C, and concentrated to obtain 1500 g of ethanol extract; The ethanol extract was suspended in 3.5L of water, and then extracted three times with equal volumes of cyclohexane, ethyl acetate, and n-butanol successively, and each extract was collected and concentrated to obtain 130.3g of cyclohexane respectively. Extract LJH, 93.7g ethyl acetate extract LJE, 199.8g n-butanol extract LJB; Get 83.0g described ethyl acetate extract LJE, dissolve with chloroform and methanol, take by weighing 120g column chromatography silica gel (100- 200 mesh) to mix the sample, and weigh 1500g of column chromatography silica gel (100-200 mesh), dissolve the silica gel with dichlo...

Embodiment 3

[0046] In vitro tumor inhibitory activity experiment of embodiment 3 (5,7,8,4'-tetrahydroxyflavone)-3'-4-(5,7-dihydroxyflavone)

[0047] The inventors carried out an in vitro anti-tumor activity test of the compound (5,7,8,4'-tetrahydroxyflavone)-3'-4-(5,7-dihydroxyflavone), in which the tumor strain was liver cancer SMCC 7721 cells .

[0048] MTT method: Inoculate SMCC 7721 cells in a 96-well cell culture plate, 200 μL per well (containing 2.5×10 4 tumor cells), at 37°C, 5% CO 2 In the incubator, and in the RPMI1640 medium containing 10% FBS, culture 24h, add the compound of the present invention of different concentrations (100, 50, 25, 12.5 and 6.25), continue to cultivate 48h; Add 20 μ L of MTT 4h before the end of the experiment (5mg / mL), continue at 37°C, 5% CO 2 Incubate under the conditions for 4 hours, add 150 μL of dimethyl sulfoxide after absorbing the culture solution, shake until the crystals are completely dissolved, and then detect the absorbance in a micropl...

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Abstract

The invention provides a biflavonoid compound. The compound has a structural formula shown in the description. The invention also provides a preparation method of the biflavonoid compound, and relatesto a pharmaceutical preparation containing the biflavonoid compound and an application of the biflavonoid compound in preparation of a medicine for treating hepatocellular carcinoma and a medicine for protecting liver. According to the compound provided by the invention, as a natural small-molecule compound, (5,7,8,4'-tetrahydroxyflavone)-3'-4-(5,7-dihydroxyflavone) has lower toxicity to normal cells and less side effects; in addition to a good function of protecting the liver, the biflavonoid compound also exhibits significant hepatocellular carcinoma-resistant effects, and the biflavonoid compound can provide a novel therapeutic medicine and therapeutic route for patients with the hepatocellular carcinoma, and has the advantages of a moderate effective dose and significant curative effects, small toxic and side effects; therefore, the biflavonoid compound has broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a biflavonoid compound, a preparation method of the biflavonoid compound, a pharmaceutical preparation containing the biflavonoid compound, and the preparation of the biflavonoid compound for treating liver cancer. Drugs, liver-protecting and liver-protecting drugs. Background technique [0002] The liver is an important organ in the human body that mainly focuses on metabolic functions, and plays a role in the body such as deoxidation, storage of glycogen, and synthesis of secreted proteins. The liver has a biotransformation effect on many non-nutritive substances from the body and outside the body, such as various drugs, poisons, and certain metabolites in the body, and completely decomposes them through metabolism or excretes them in their original form. This effect is also called " detoxification function". It can be seen that the liver is the most i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D311/40A61K31/352A61P35/00A61P1/16
Inventor 曾小斌葛兰兰李华英朱富强李洁媚万浩强周伯平吴诗品
Owner SHENZHEN PEOPLES HOSPITAL
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