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An ent-kaurane diterpene derivative and applications thereof

A technology of kaurane diterpene and derivatives, which is applied in the field of corresponding-kaurene diterpene derivatives and its application, and can solve the problem of narrow anti-cancer spectrum

Inactive Publication Date: 2018-04-17
TIANJIN PEOPLE HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Chinese patent application CN106631804A discloses a corresponding-kaurane diterpene derivative extracted from a plant of the genus Camellia as follows: (Isoforresin A, referred to as Iso A), and pointed out that IsoA is a thioredoxin-1 (thioredoxin-1, referred to as Trx-1) inhibitor, which has a certain inhibitory effect on some tumor cells and can prolong the survival of liver cancer tumor-bearing mice. However, the experimental results show that the anti-cancer spectrum of IsoA is narrow, and it is only effective for a few types of tumors such as liver cancer.

Method used

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  • An ent-kaurane diterpene derivative and applications thereof
  • An ent-kaurane diterpene derivative and applications thereof
  • An ent-kaurane diterpene derivative and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0019] The extraction of embodiment 1 formula (I) compound

[0020] The preparation method of formula (I) compound, comprises the following steps:

[0021] (1) Get the plant aboveground part of the leaf-scroll tea plant and dry it in the shade and pulverize it into a plant powder;

[0022] (2) Soak the plant powder obtained in step (1) with a mixed solvent of ethanol and petroleum ether at a volume ratio of 3.5 to 5:1, reflux and extract at below 50°C for 2 to 4 hours, cool down and separate the solid part to obtain an extract, mix the solvent with the plant The weight ratio of powder is 5~10:1

[0023] (3) controlling the leach solution obtained in step (2) to be concentrated under reduced pressure at 50° C. to become a crude product extract,

[0024] (4) in step 3) obtain medicinal extract and process decolorization through macroporous adsorption resin, obtain medicinal extract, obtain medicinal extract by silica gel column chromatography to obtain compound (I) the describ...

Embodiment 2

[0049] Pharmacological Example 2 The Inhibitory Effect of Formula (I) Compounds on Different Types of Solid Tumor Cells

[0050] The compound of formula (I) (purity>99%) was dissolved in DMSO, and a 100uM mother solution was prepared and stored at -20°C. Select ten common malignant solid tumors (including lung cancer, gastric cancer, breast cancer, colorectal cancer, liver cancer, cervical cancer, esophageal cancer, oral cancer, prostate cancer, pancreatic cancer), and culture the tumor cell lines of the above ten tumors in vitro and among them The corresponding tissue normal cell lines of the five tumors are as follows:

[0051] Lung cancer: human normal lung epithelial cells HBEC, human lung cancer cells A549, SK-MES-1

[0052] Gastric cancer: human normal gastric mucosal epithelial cells RGM-1, human gastric cancer cells MGC-803, SGC-7901

[0053] Breast cancer: human normal breast epithelial cells MCF10A, human breast cancer cells MCF7, MDA-MB-231

[0054] Colorectal ca...

Embodiment 3

[0066] Pharmacological Example 3, Comparative Test on the Survival Period of Tumor-bearing Mice

[0067] 1. Materials

[0068] a) Cell line: Gastric cancer cell MGC-803, which can stably express luciferase, was purchased from the Cell Bank of the Type Culture Collection Committee of the Chinese Academy of Sciences.

[0069] b) Animals: 20 BALB / c nude mice, body weight (13±2g), male.

[0070] c) Drug: Iso A (drug 1), formula (I) compound (drug 2)

[0071] 2. Experimental method

[0072] a) Preparation of gastric cancer tumor-bearing mouse model: Gastric cancer cells MGC-803 in the logarithmic growth phase were taken, digested with trypsin and prepared into 1×10 7 cells / mL cell suspension, inoculate 200 μL (100 μl cells + 100 μl Matrigel) cell suspension into the right axilla of nude mice (only 200 μL Matrigel was injected in the normal group).

[0073] b) Grouping and administration of experimental animals: After two weeks of feeding, the tumor-bearing situation in the mice...

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Abstract

An ent-kaurane diterpene derivative and applications thereof are disclosed. The derivative is shown as a formula (I). A preparing method of the compound of the formula (I) includes (1) drying an overground part of rabdosia phyllostachys (Diels) Hara in shade, and then crushing the overground part into plant powder; (2) soaking the plant powder obtained in the step (1) by a mixed solvent includingethanol and petroleum ether in a volume ratio of 3.5-5:1, performing reflux extraction at 50 DEG C for 2-4 h, cooling, and separating a solid part to obtain a leachate, with the weight ratio of the mixed solvent to the plant powder being 5-10:1; (3) subjecting the leachate to vacuum concentration at 50 DEG C to obtain crude extract; and (4) decoloring the extract obtained in the step (3) through macroporous adsorptive resin to obtain extract, and subjecting the extract to column chromatography on silica gel to obtain the compound of the formula (I).

Description

Technical field: [0001] The invention relates to a novel diterpene compound and its application in the preparation of antitumor drugs. Background technique: [0002] Chinese patent application CN106631804A discloses a corresponding-kaurane diterpene derivative extracted from a plant of the genus Camellia as follows: (Isoforresin A, referred to as Iso A), and pointed out that IsoA is a thioredoxin-1 (thioredoxin-1, referred to as Trx-1) inhibitor, which has a certain inhibitory effect on some tumor cells and can prolong the survival of liver cancer tumor-bearing mice. However, the experimental results show that the anti-cancer spectrum of IsoA is narrow, and the therapeutic effect on only a few types of tumors such as liver cancer is obvious. Therefore, it is an urgent problem to be solved in the prior art to continue to screen new natural compounds with new anti-cancer spectrum from Camellia drugs. Contents of the invention [0003] In the study, we found that a new cor...

Claims

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Application Information

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IPC IPC(8): C07C67/48C07C69/21A61K31/22A61P35/00
CPCC07B2200/07C07C67/48C07C69/21
Inventor 张春泽王文虹王弋嘉张恒
Owner TIANJIN PEOPLE HOSPITAL
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