143839-02-5Relevant articles and documents
Method for preparing asiatic acid by hydrolyzing asiaticoside
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Paragraph 0017-0032, (2017/08/27)
The invention discloses a method for preparing asiatic acid by hydrolyzing asiaticoside. The method comprises the following steps: 1) mixing asiaticoside, lauryl sodium sulfate and NaOH, adding water for dissolution, and hydrolyzing at normal temperature for 10-15 minutes; 2) regulating the pH value of the hydrolysate to 2-5, standing, filtering, and collecting the precipitate; and 3) dissolving the precipitate in ethanol, filtering, adding water to the filtrate, crystallizing, filtering to obtain the crystal, and drying to obtain the finished product. The method can quickly cut off glycosidic bonds under the conditions of normal temperature and pressure, has the advantages of mild hydrolytic process and thorough hydrolysis, and can not generate configurative changes of asiatic acid.
Synthesis, antiproliferative and apoptosis-inducing effects of novel asiatic acid derivatives containing α-aminophosphonates
Huang, Ri-Zhen,Wang, Cai-Yi,Li, Jian-Fei,Yao, Gui-Yang,Pan, Ying-Ming,Ye, Man-Yi,Wang, Heng-Shan,Zhang, Ye
, p. 62890 - 62906 (2016/07/16)
A series of novel asiatic acid (AA) derivatives containing α-aminophosphonate were designed and synthesized as antitumor agents. In vitro antitumor activities of these compounds against five cancer cell lines (A549, Hct-116, T24, Spca-2 and SK-OV-3 cell) and a normal cell line (HUVEC cell) were evaluated, employing standard MTT assay. Antitumor activities screening result indicated that many target compounds displayed moderate to high levels of antitumor activities compared with AA, 5-fluorouracil (5-FU) and cisplatin, and exhibited much lower cytotoxicity against normal cell than 5-FU and cisplatin. In addition, the mechanism of representative compound 3d was preliminarily investigated by AO/EB staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining, flow cytometry and western blot. Compound 3d inducing apoptosis involved intracellular Ca2+ production, the loss of mitochondrial membrane potential and intracellular reactive oxygen species (ROS) production. Western blot analysis also demonstrated that compound 3d treatment triggered the mitochondrial apoptotic pathway, indicating by changing Bax/Bcl-2 ratios, cytochrome c release, and caspase-9 activation. Moreover, the cell cycle analysis showed that compound 3d may confine T24 cells in G1/S phase mainly through the p53-dependent pathway. Together, these results implied a critical role of ROS, caspase-9 and p53 in compound 3d-inducing G1/S arrest and apoptosis of T24 cells.
Design, synthesis, and biofunctional evaluation of novel pentacyclic triterpenes bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety as antiproliferative agents
Zhao, Chun-Hui,Zhang, Cui-Li,Shi, Jin-Jie,Hou, Xi-Yan,Feng, Bin,Zhao, Long-Xuan
, p. 4500 - 4504 (2015/10/12)
A series of pentacyclic triterpenoids derivatives bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety has been synthesized and investigated for their potential antiproliferative activities. Pentacyclic triterpenoids derivative compounds were synthesized by a four or six step synthetic procedure. The activity studies were evaluated using Cell Counting Kit-8 method, and Western blotting analysis on A549 cells, MCF-7 cells and Hela cells. Compounds methyl 3-O-[4-(1-piperazinyl)-4-oxo-butyryl]olean-12-ene-28-oate (OA-4) and compound 2-O-[4-(1-piperazinyl)-4-oxo-butyryl]-3,23-dihydroxyurs-12-ene-28-oate (AA-5) were found to be promising antiproliferative agents. These compounds show potentiality for further optimization as antitumor drugs.
