Preparation and medical application of stevanate a and its derivatives

A kind of alkaloid ester and fenestrate technology are applied in the application field of preparing antitumor drugs, and can solve the problems of no research report on the chemical composition of alkaloid, no record of medicinal use of alkaloid, etc.

Active Publication Date: 2017-08-04
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no medicinal record of aster asteroid in the literature, and there is no research report on the chemical composition of aster asteroides

Method used

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  • Preparation and medical application of stevanate a and its derivatives
  • Preparation and medical application of stevanate a and its derivatives
  • Preparation and medical application of stevanate a and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 Extraction and separation from plants to prepare asteryl asterate A

[0068] (1) Extraction, separation and purification of stevanate A:

[0069] Cut the whole herb of dried Aster asteroides into small sections and pulverize it into powder (1.5 kg) with a traditional Chinese medicine pulverizer, extract 3 times with methanol percolation (5000 milliliters for 12 hours for the first time, and 4000 milliliters for 5 hours each for the other times), The methanol percolation solution was combined and then concentrated under reduced pressure to obtain concentrated methanol extract (1000 ml). The concentrated methanol extract was extracted 3 times with cyclohexane (500 ml each time), and the combined cyclohexane extract was decompressed. Concentration gave cyclohexane extract extract (12.5 g). The cyclohexane extract extract was separated by silica gel column chromatography, and eluted sequentially with cyclohexane / ethyl acetate (9:1 and 4:1, v / v), and cyclohexane / e...

Embodiment 2

[0072] Example 2 Chemical Synthesis Preparation of Stennate A and Derivatives of Stennyl A

[0073] (1) Preparation of coniferic acid (3): 36.51 grams of vanillin (3a, 0.24mol), 31.22 grams of malonic acid (3b, 0.30mol), 60mL of dioxane, 30mL of anhydrous pyridine, and 3mL of aniline , keep the reaction at 90-95°C for 3 hours, cool to room temperature, add 200mL of 20% potassium carbonate and stir, adjust the pH to 2-3 with concentrated hydrochloric acid, precipitate the precipitate, filter it with suction, wash the solid with cold water, and dry it in vacuum Obtain coniferic acid (3,41.96 g) in the form of pale yellow-white powder. Molecular formula: C 10 h 10 o 4 ; 1 H-NMR data (500MHz, methanol-d 4 ): δ7.13(1H,d,J=1.9Hz,H-2),7.03(1H,dd,J=8.2 / 1.9Hz,H-6),6.80(1H,d,J=8.2Hz,H -5),7.57(1H,d,J=15.9Hz,H-7),6.28(1H,d,J=15.9Hz,H-8),3.86(3H,s,OCH 3 -3); HRESIMS m / z[M+Na] + 217.0452 (calculated value C 10 h 10 NaO 4 ,217.0477).

[0074] (2) Preparation of methyl coniferate...

Embodiment 3

[0097] Example 3 Inhibitory effect of stevanate A and its derivatives on the proliferation of glioma cells

[0098]Human glioma U87-MG and U251 cells were cultured with DMEM and 10% FBS medium in an incubator at 37°C and 5% carbon dioxide. Intestinal cancer HCT-15 cells were cultured with RPMI-1640 medium in an incubator at 37°C and 5% carbon dioxide, while intestinal cancer SW620 cells were cultured in a 37°C incubator with Leibovitz's L15 medium. All cells cultured for three generations were used for the experimental research of the present invention, and doxorubicin (DOX) and Temozolomide (TMZ), the first-line drug currently clinically used to treat glioma, were used as positive controls.

[0099] The survival rate of tumor cells was determined by the sulforhodamine B method (SRB). Cells were seeded in 96-well plates, and different concentrations of test drugs were added 24 hours after adherence. After 72 hours of drug treatment, stain with SRB, measure the absorbance at ...

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PUM

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Abstract

The invention provides a preparation method for extracting and separating tripolinolate A from herb of Tripolium vulgare Nees, and synthesizing tripolinolate A and a derivative thereof. The tripolinolate A and the derivative thereof substantially inhibit proliferation of human glioma U87-MG and U251 and intestinal cancer HCT-15 and SW620 cells, induces tumor cell apoptosis, and can be used to prepare tumor treatment medicines. The tripolinolate A and the derivative thereof have effects on colloid tumors and the intestinal cancer, and also have effects on other tumors and cancers. The structural general formula of the tripolinolate A and the derivative thereof is shown in the specification.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to the preparation and medical application of antitumor active compound tripolinolate A (tripolinolate A) and derivatives of tripolinolate A. More specifically, it is extracting and separating stevanate A from plant aster (Tripolium vulgare Nees), preparing stevanate A and derivatives of stevanate A by chemical synthesis, and their application in the preparation of antitumor drugs. Background technique [0002] Tripolium vulgare Nees is the only plant of the genus Tripolium in the Asteraceae family. It is distributed in Europe, Asia, North America and northern Africa, in my country's Jilin, Shanxi, Inner Mongolia, Shaanxi, Gansu, Xinjiang, Shandong, Jiangsu , Zhejiang and other provinces are distributed. Aster is an obligate halophyte in the temperate climate zone, and it mostly grows in low-lying saline-alkali spots, coasts of saline-alkali wetlands, lakesides and swamps. At present, there i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/222A61P35/00C07C67/48C07C67/08C07C69/28C07C69/16
Inventor 张治针陈璐梁英宋腾飞安佳库玛王文玲虞斯然黄豪彩连晓媛
Owner ZHEJIANG UNIV
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