Method for preparing anti-tumor lead compound Tagalsin C by utilizing tagalsin E and Tagalsin G

Abstract

The invention discloses a method of preparing anti-tumor lead compound Tagalsin C by utilizing Tagalsin E and Tagalsin G. The method comprises the following steps of: (1) adding Tagalsin E and potassium tert-butoxide into a reaction container and adding anhydrous tetrahydrofuran; vacuumizing the container and ventilating oxygen gas, and stopping the reaction after reacting for 10 hours under -15 DEG C; (2) adding Tagalsin G and palladium acetate into the reaction container and then adding anhydrous dimethyl sulfoxide, vacuumizing the container and ventilating oxygen gas, and stopping the reaction after reacting for 24 hours under 60 DEG C; and (3) extracting the final products obtained in the reaction of (1) and (2) by ethyl acetate, and eluting by using petroleum ether / ethyl acetate as a mobile phase through positive-phase silica gel column chromatography and purifying to obtain Tagalsin C. The preparation method disclosed by the invention is less in steps, high in yield, small in environmental pollution, green and environment-friendly.

Description

technical field [0001] The invention relates to a method for preparing anti-tumor active lead compound Tagalsin C by using diterpenoids Tagalsin E and Tagalsin G, belonging to the technical field of pure chemistry. Background technique [0002] Tagalsin C is a dolabrane-type diterpenoid isolated from Ceriops tagal for the first time in 2005 (Yan Zhang, Wenhan Lin, et al. Phytochemistry, 2005, 66: 1465-1471). According to reports, the compound has membrane permeability and broad-spectrum anti-tumor activity, and can kill human promyelocytic acute leukemia cells HL-60, human myeloma cells TM9, human acute T-cell leukemia cells Jurkat, human macrophage lymphocytes Tumor cell U937, human lung cancer cell A549, human breast cancer cell MCF-7 and MDA-MB-231, human liver cancer cell HepG2, human prostate cancer cell PC-3 and human cervical cancer epithelial cell Hela, while normal cells human kidney embryo Cell 293 and human liver diploid cell L02 have no obvious killing ability, ...

AI Technical Summary

Problems solved by technology

However, the source of Tagalsin C is currently limited to extraction and isolation from the mangrove plant silique, and the extraction process is complicated, which greatly increases the drug development cost of Tagalsin C

However, the diterpenoids Tagalsin E and Tagalsin G, which are structurally similar, are abundant in siliques (Tagalsin E is 7 to 10 times that of Tagalsin C, and Tagalsin G is 15 to 20 times that of Tagalsin C), but they do not have Tagalsin Significant anticancer activity of C

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