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Polymerization aaptamine alkaloid compounds, preparation method thereof and application of polymerization aaptamine alkaloid compounds

A technology of compounds and alkaloids, applied in the field of medicine, can solve problems such as no anti-tumor activity.

Inactive Publication Date: 2012-11-21
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few research reports on the chemical constituents of the Aaptos suberitoides sponge. Only people such as Sachiko Tsukamoto of Kumamoto University in Japan extracted three known chemical constituents of aaptamine, isoaaptamine and demethylaaptamine from the Indonesian sponge Aaptos suberitoides in 2010 (Tsukamoto S., Yamanokuchi R., Yoshitomi M., Sato K., Ikeda T., Rotinsulu H., Mangindaan R.E.P., Voogd N.J.de, Soest R.W.M.van, Yokosawa H. Aaptamine, an alkyloid from the sponge Aaptos suberitoides, functions as a proteasome inhibitor. Bioorganic & Medicinal Chemistry Letters, 2010, 11, 3341-3343), there is no report that the polymeric aaptamine alkaloid compound isolated from this kind of sponge has anti-tumor activity

Method used

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  • Polymerization aaptamine alkaloid compounds, preparation method thereof and application of polymerization aaptamine alkaloid compounds
  • Polymerization aaptamine alkaloid compounds, preparation method thereof and application of polymerization aaptamine alkaloid compounds
  • Polymerization aaptamine alkaloid compounds, preparation method thereof and application of polymerization aaptamine alkaloid compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the separation and extraction of compound I-VII

[0044] 1. Obtaining the extract

[0045] After crushing the sponge sample (wet weight 2.0kg) frozen and stored, it was extracted by dynamic cold immersion with methanol three times at room temperature, soaked for 3 days each time; Total extract 80g.

[0046] 2. Separation and purification of compounds

[0047]After the extract (80.0 g) was dissolved with methanol solvent, add 80 g of 100-200 mesh silica gel (Qingdao Ocean Chemical Group Co., Ltd. product) to mix the sample, remove the solvent under reduced pressure, and use silica gel column chromatography to analyze the mixture with 100% sherwood oil, petroleum Ether-acetone (20:1, 15:1, 10:1, 5:1, 3:1, 2:1, 1:1), 100% acetone, 100% methanol as solvent for gradient elution, divided into 8 share. Fr-6 (2.5 g, petroleum ether-acetone 1:1 eluate) was subjected to forward silica gel column chromatography, with petroleum ether / acetone (6:1, 3:1, 2:1, 1:1) g...

Embodiment 2

[0098] Embodiment 2: the test of antitumor activity in vitro

[0099] Cell Proliferation Inhibitory Activity Test

[0100] 1. Experimental samples and experimental methods

[0101] Preparation of the test sample solution: the test sample is the pure compound I-VII isolated and refined in Example 1 above. Accurately weigh an appropriate amount of sample, and prepare a solution with the required concentration with methanol for activity measurement.

[0102] Cell lines and subculture of cells: Human liver cancer BEL-7402 cells, human cervical cancer HeLa cells, chronic myelogenous leukemia K562 cells, mouse leukemia P388 cells and other cancer cell lines are used. All kinds of cells were subcultured in RPMI-1640 medium containing 10% FBS at 37°C in an incubator filled with 5% carbon dioxide.

[0103] Cell Proliferation Inhibitory Activity Test Method

[0104] Lissamine rhodamine B (SRB) method: Take human cervical cancer HeLa cells and human liver cancer BEL-7402 cells in the...

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Abstract

The invention relates to the technical field of medicines, in particular to 7 novel dimerization and trimerization aaptamine alkaloid compounds having antineoplastic activity. The 7 novel dimerization and trimerization aaptamine alkaloid compounds are separated from sponge Aaptos suberitoides (1934) collected in the South Sea of China. Vitro antineoplastic activity experiments show that the alkaloid compounds has evident inhibition effect to tumor cells such as K562 (chronic myelocytic leukemia) and P388 (mouse leukemia cells) and can be used to prepare antineoplastic drugs. By the alkaloid compounds, lead compounds for researching novel antineoplastic drugs are provided, and development and utilization of marine medicinal resources are facilitated.

Description

Technical field: [0001] The invention relates to the technical field of medicine. Specifically related to the sponge Aaptos suberitoides ( 1934), seven new dimeric and trimeric aaptamine alkaloid compounds with anti-tumor activity and their preparation methods and applications. Background technique: [0002] Sponges are extremely abundant multicellular animals in the ocean, and the research on them has been very active at home and abroad in recent years. Aaptos sponges belong to the class Demospongiae, the order Hadromerida, and the family Suberitidae. So far, the chemical composition of more than 20 kinds of sponges in this genus has been studied. The main characteristic composition is aaptamine alkaloid with benzo[de][1,6]-naphthyridine as the skeleton. This type of alkaloid mainly has anti-tumor, Antibacterial, antiviral, antidepressant, and enzyme inhibitory activities (see Larghi, E.L., Bohn, M.L., Kaufman, T.S. Aaptamine and related products. Their isolation, chemi...

Claims

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Application Information

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IPC IPC(8): C07D519/00A61K31/4745A61P35/00
Inventor 李国强刘彩霞唐旭利李平林
Owner OCEAN UNIV OF CHINA
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