35959-01-4Relevant academic research and scientific papers
Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells
Leal, Ana S.,Wang, Rui,Salvador, Jorge A.R.,Jing, Yongkui
, p. 5774 - 5786 (2012/11/06)
A series of new heterocyclic derivatives of ursolic acid 1 were synthesized and evaluated for their antiproliferative activity against AsPC-1 pancreatic cancer cells. Compounds 24-32, with an α,β unsaturated ketone in conjugation with an heterocyclic ring in ring A have improved antiproliferative activities. Compound 32 is the most active compound with an IC50 of 1.9 μM which is sevenfold more active than ursolic acid 1. Compound 32 arrests cell cycle in G1 phase and induces apoptosis in AsPC-1 cells with upregulation of p53, p21waf1 and NOXA protein levels.
Synthesis and in vitro cytotoxicity of novel ursolic acid derivatives
Meng, Yanqiu,Song, Yanling,Yan, Zhaokai,Xia, Yan
experimental part, p. 4033 - 4040 (2010/10/03)
In an effort to improve potential hepatoprotective and anti-tumor activities, eight novel ursolic acid (UA) derivatives were designed and synthesized with substitution at positions of C-3, C-11and C-28 of UA. Their structures were confirmed using IR, MS and 1H-NMR and elemental analysis. Their in vitro cytotoxicity against various cancer cell lines (HeLa, SKOV3 and BGC-823) was evaluated by the standard MTT assay. Among them, compound 13 exhibited more potent cytotoxicity than ursolic acid.
Oxyfunctionalization products of terpenoids with dimethyldioxirane and their biological activity
Ogawa, Shoujiro,Hosoi, Keiji,Ikeda, Noriaki,Makino, Mitsuko,Fujimoto, Yasuo,Iida, Takashi
, p. 247 - 250 (2007/10/03)
Oxyfunctionalization of the bioactive terpenoids, ursolic acid acetate (1), oleanolic acid acetate (5), lupeol acetate (12), and kaurenic acid (17), with dimethyldioxirane (DMDO) was investigated. Treatment of the terpenoids with DMDO under mild conditions afforded a variety of oxidation and oxydegradation products to yield naturally occurring and/or novel compounds in one step. After chromatographic separation, the structures of the individual isolated products were determined using spectroscopic methods including several homonuclear ( 1H-1H) and heteronuclear (1H-13C) shift-correlated 2D-NMR techniques. The inhibitory activity of the terpenoid derivatives against α-glucosidase was investigated and compounds 1, 3, 7, and 9 were found to exhibit potent activity.
PROLONGED TREATMENT OF ACETYLMETHYL URSOLIC ACID WITH H2O2/ACETIC ACID - A FACILE ONE-POT SYNTHESIS OF 15α-HYDROXY ANALOGUE
Siddiqui, Salimuzzaman,Siddiqui, Bina Shaheen,Adil, Qayyum,Begum, Sabira
, p. 3569 - 3580 (2007/10/02)
With a view to obtain new compounds bearing potential applications in the biogenetic type synthesis of natural products, acetylmethyl ursolic acid (1) was subjected to prolonged treatment with H2O2/AcOH on boiling water bath.Several such products (2, 3, 5 and 7) have thus been obtained.A new one-pot partial synthesis of 15α-hydroxy Δ12-analogues of pentacyclic triterpenes of amyrin series has been achieved. 13C-NMR spectral data of the major product are also described.
Phase-transfer Catalysed Oxidation with Chromic Trioxide: A Simple Procedure for Allylic Oxidation in α-Amyrin and β-Amyrin Series
Singh, Chandan
, p. 300 - 301 (2007/10/02)
Oxidation of α-amyrin acetate (3), β-amyrin acetate (1), ursolic acid acetate (5), hederagenin diacetate (7) and brahmic acid triacetate (9) by aqueous chromic trioxide in the presence of cetyltrimethylammonium bromide as phase-transfer catalyst in CCl4 furnishes the 11-oxo derivatives in more than 80percent yield.
