Indole diketopiperazine alkaloid compound derived from tryptophan and proline, preparation method and use thereof

A compound, the technology of use, and the field of use in the preparation of a cell proliferation inhibitor, a cell apoptosis inducer or an antitumor agent

Inactive Publication Date: 2011-12-07
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have found that indole diketopiperazine alkaloids derived from tryptophan and proline have anti-tumor activity. Currently, there are relatively few reports on the chemical structure and cell proliferation inhibition of these compounds in the trans relative configuration. Rare, and there are no related drugs on the market

Method used

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  • Indole diketopiperazine alkaloid compound derived from tryptophan and proline, preparation method and use thereof
  • Indole diketopiperazine alkaloid compound derived from tryptophan and proline, preparation method and use thereof
  • Indole diketopiperazine alkaloid compound derived from tryptophan and proline, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Fermentative production and separation and purification of embodiment 1 compound I

[0011] 1 Fermentation production

[0012] Fermentation culture of production bacterium: according to the conventional method of cultivating microorganisms, get Taichung Aspergillus ZHN-7-07 (Aspergillus taiichungensis ZHN-7-07) (preservation number is: CCTCC M 2010354) in an appropriate amount, inoculate on the PDA solid slant medium, Cultivate for 4 days in a 28°C incubator.

[0013] Take an appropriate amount of Taichung Aspergillus ZHN-7-07 (Aspergillus taichungensis ZHN-7-07) that has been cultured on a slant for 4 days, and inoculate it into 80g of rice medium [medium composition: rice 80.0g, water 120mL, seawater 6.7g, pH Naturally] in the 1000mL Erlenmeyer flask, under 28 degree centigrade conditions static culture 30 days, obtain fermentation product.

[0014] 2 Obtaining the extract

[0015] The rice fermentation product was soaked and extracted three times with methanol, ce...

Embodiment 2

[0025] The test of embodiment 2 in vitro antitumor activity

[0026] Cell Proliferation Inhibition Activity Test and Cell Apoptosis Induction Activity Test

[0027] 1 Experimental samples and experimental methods

[0028] Preparation of the test sample solution The test sample is the pure compound I isolated and refined in the above-mentioned Example 1. Accurately weigh an appropriate amount of sample, and prepare a solution with the required concentration with methanol for activity measurement.

[0029] Cell lines and subculture of cells adopt cancer cell lines such as human lung cancer A-549 cells and human leukemia HL-60 cells. All kinds of cells were subcultured in RPMI-1640 medium containing 10% FBS at 37°C in an incubator filled with 5% carbon dioxide.

[0030] Cell Proliferation Inhibitory Activity Test Method

[0031] Human lung cancer A-549 cells in the logarithmic growth phase were obtained by the Lissamine rhodamine B (SRB) method, and prepared with fresh RPMI-1...

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Abstract

The invention relates to an indole diketopiperazine alkaloid compound derived from tryptophan and proline and a preparation method and application thereof. In the method, the indole diketopiperazine alkaloid compound which has a novel structure and is derived from tryptophan and proline is produced from Aspergillus taichungensisZHN-7-07 extracted from a mangrove forest brined eastern bracken fern rhizome mud sample. As proved by an experiment, the indole diketopiperazine alkaloid compound can be taken as a cell proliferation inhibitor, a cell apoptosis inducer or an antineoplastic agent.

Description

Technical field: [0001] The present invention relates to using Taichung Aspergillus ZHN-7-07 (Aspergillus taichungensis ZHN-7-07) (preserved in Wuhan University China Type Culture Collection Center on December 22, 2010, the preservation number is: CCTCC M 2010354) to produce tryptophan containing A method for the indole diketopiperazine alkaloid compound of acid and proline; the present invention also relates to the use of this type of compound in the preparation of cell proliferation inhibitors, apoptosis inducers or antitumor agents. Background technique: [0002] Indole diketopiperazine alkaloids derived from tryptophan and proline are mainly a class of indole alkaloids produced by microorganisms, which are based on a molecule of tryptophan and a molecule of proline The diketopiperazine alkaloid Brevianamide F formed by acid is the basic core. Due to the existence of the indole ring aromatic system in the molecular structure, it has multiple structural modification sites...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22A61K31/4995A61P35/00C12P17/18C12R1/66
Inventor 顾谦群蔡生新李德海朱天骄
Owner OCEAN UNIV OF CHINA
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