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Novel flavonoid extracted from Maackia amurensis

A technology of flavonoids and compounds, applied in the field of medicine

Inactive Publication Date: 2009-05-20
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

7 compounds described in the present invention have not yet been reported

Method used

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  • Novel flavonoid extracted from Maackia amurensis
  • Novel flavonoid extracted from Maackia amurensis
  • Novel flavonoid extracted from Maackia amurensis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] Embodiment 1: the preparation of compound 1-7

[0009] 1. Extraction and separation

[0010] Take 9 kg of dried pagoda tree bark, heat and reflux extract with 70% ethanol for 4 times, each time for 3 hours, dry under reduced pressure, concentrate to obtain 1800 g of extract. The medicinal extract is suspended in water, and in a ratio of 1:1, it is extracted successively with sherwood oil, ethyl acetate, and n-butanol, and each solvent is extracted 3 times, and the extracted part is concentrated under reduced pressure respectively to obtain 120 g of the sherwood oil extracted part. Carry out silica gel column chromatography (800g, 200-300 mesh), use petroleum ether-dichloromethane (10:1→1:1), dichloromethane-ethyl acetate gradient elution (50:1→1:1), A total of 109 fractions were collected, each with a volume of about 500 mL, and combined according to thin-layer chromatography to obtain 9 sub-fractions (Fr.1-Fr.9). Fr.3 by Sephadex LH-20 gel chromatography, CH 2 Cl 2...

Embodiment 2

[0028] Example 2: Confirmation of the structure of compound 1-7

[0029] Table 1. Physicochemical constants and main spectral data of compounds 1-7

[0030] Compound 1

[0031] Molecular formula C 26 h 28 o 6 , It is a white amorphous powder. [α] 20 D =-67.3° (c, 0.1, MeOH), CD (c0.05, MeOH; nm): [θ] 350 +0.92, [θ] 290 -6.20. UV(MeOH) has maximum absorption at 289nm. IR(KBr)υ max , cm -1 3443 (broad), 2925, 1634, 1502, 1445, 1383, 1206, 1167, 1106, 1073. ESI-MSm / z: 437.3[M+1] + , 435.3[M-1] - , 873.8[2M+1] + , 871.6[2M-1] - , HR-ESI-MS m / z 437.1968[M+H] + . 1 HNMR (600MHz, acetone-d 6 ) see Table 2. 13 CNMR (150MHz, acetone-d 6 ) see Table 2.

[0032] Compound 2

[0033] Molecular formula: C 30 h 34 o 5 , Pale yellow jelly. [α] 20 D = -34.7° (c, 0.2, MeOH). UV(MeOH) has maximum absorption at 293nm. IR(KBr)υ max cm -1 3420, 2973, 2923, 1637, 1505, 1435, 1383, 1170, 1148, 1077. ESI-MSm / z: 475.4[M+1] + , 473.4[M-1]- , HR-ESI-MS m / z 475.2480[M+H]...

Embodiment 3

[0052] Example 3: Antitumor activity of compounds 1-7

[0053] The in vitro antitumor activity of the above compounds was investigated by MTT method. The specific implementation method is as follows:

[0054] Human cervical cancer HeLa cells, human melanoma A375S2 cells, human breast cancer MCF-7 cells, and human liver cancer HepG2 cells were seeded in 96-well plates at a density of 1×105 / well, and after 12 hours of culture, samples of different concentrations were added to continue the culture. After 48 hours, the culture solution was discarded, and 100 μl of culture solution and 10 μl of 5 mg / ml MTT were added to each well, and cultured for another 4 hours, and the absorbance was measured with an enzyme-linked immunoassay analyzer. At the same time, a blank control and a negative control were set, and 5-fluorouracil was used as a positive control, and the mortality rate was calculated according to the following formula:

[0055]

[0056] The IC of each compound was calc...

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Abstract

The invention pertains to the technical field of medicaments, and relates to a new flavonoid compound extracted from Maackia amurensis. The invention uses various separation methods including silica gel column chromatography, macroporous adsorptive resins, sephadex LH-20 column chromatography, semi-preparation type high-efficiency liquid chromatography, and the like. 54 compounds and 14 flavonoid compounds are seperated from the maackia amurensis, wherein, 7 new chemical components are included, which are respectively Maackiaflavanone A, Maackiaflavanone B, Maackiapentone, Maackiapterocarpan A, Maackiapterocarpan B, Maackiaisoflavonoside and 8-3, 3-dimethylallyl-5-hydroxy-7-methoxy chromone. A preliminary activity study indicates that the compound has certain effect of inhibiting the proliferation of tumor cells, thereby providing a basis for the development and research in the future.

Description

technical field [0001] The invention belongs to the technical field of medicine, relates to new flavonoids extracted from pagoda japonica, and also relates to an extraction and separation method and application of the new flavonoids extracted from pagoda japonica. Background technique [0002] North Korean locust tree (Maackia amurensis Rupr. et Maxim.), also known as mountain locust tree, Korean locust tree, and Huai locust tree, is a plant of the genus Saddle Tree in the family Fabaceae. Korean Sophora japonica is a folk medicine, its stems and branches have the effect of dispelling rheumatism, and can be used for the treatment of rheumatoid arthritis; the Korean people use the leaves and branches of Korean Sophora japonica to treat tumors; the folks of the Russian Amur state use the leaves and branches of Korean Sophora japonica The skin of the tree is used to treat liver disease and cholecystitis; the Jina people in the Russian Far East use the powdered inner bark of Sop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/28C07D311/30C07D493/04C07D493/22C07H17/07A61K31/352A61K31/7048A61P35/00
Inventor 崔征黎雄王东张会梅代英辉
Owner SHENYANG PHARMA UNIVERSITY
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