6089-92-5Relevant articles and documents
Pentacyclic triterpene acids in olives
Bianchi,Pozzi,Vlahov
, p. 205 - 207 (1994)
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The cytotoxicity of oleanane derived aminocarboxamides depends on their aminoalkyl substituents
Kahnt, Michael,Loesche, Anne,Serbian, Immo,Hoenke, Sophie,Fischer, Lucie,Al-Harrasi, Ahmed,Csuk, René
, (2019)
Several oligo-methylene diamine derived carboxamides of oleanolic and maslinic acid have been prepared, and substitutions of the terminal primary amine as well as variations of the length of alkyl chain of the diamine moiety were made. Biological evaluation of their cytotoxic activity was performed using photometric sulforhodamin B assays employing a panel of different human cancer cell lines. These experiments showed most of the carboxamides to be cytotoxic with EC50 values below 10 μM. Prolongation of the alkyl chain length initially reduced EC50 values to a minimum, but a decrease in cytotoxicity was observed for longer alkyl chains. Variation of substituents at the terminal nitrogen atom, however, did not influence EC50 values at all. Noteworthy results were obtained particularly for compounds 4, 6 and 23 as indicated by EC50 values lower than 2 μM, and in case of a maslinic derivative 23 even an increased tumor/non-tumor cell selectivity was observed. These compounds were further investigated using fluorescence microscopy and flow cytometry analysis, which revealed 6 to show indications of apoptosis.
Interaction between the anti-cancer drug diacetyl maslinic acid and bovine serum albumin: A biophysical study
Molina-Bolívar,Galisteo-González,Carnero Ruiz,Medina-O'Donnell,Parra
, p. 304 - 313 (2015)
Steady-state and time-resolved fluorescence, as well as Fourier transform-infrared (FT-IR) spectroscopy studies were made to understand the interaction between diacetyl maslinic acid (DMA) and bovine serum albumin (BSA) at pH 7.4. A decrease in fluorescence intensity and a blue shift of the emission peak were observed in the DMA-BSA complex, which were attributed to changes in the microenvironment of the protein fluorophores. Spectroscopic analysis revealed that the fluorescence-quenching mechanism between DMA and BSA was a static procedure. Displacement experiments with site markers indicated that DMA binds to BSA at Sudlow's site I (subdomain IIA). Binding constants for the protein-drug interaction were determined at three different temperatures (298, 305, and 310 K). Enthalpy (ΔH0) and entropy (ΔS0) changes indicated that hydrophobic interactions were the dominant intermolecular forces in the binding of DMA to BSA. The interaction appears to be entropy-driven, and the process spontaneous and endothermic. Enthalpy-entropy compensation suggests that reorganization of water molecules plays an important role. Anisotropy and FT-IR experiments revealed that BSA loses its structure in the presence of DMA. The secondary structure compositions of free BSA and DMA-BSA complex were determined by FT-IR. The binding distance and transfer efficiency for DMA-BSA complex were calculated according to the F?ster theory of non-radiative energy transfer.
Pentacyclic triterpene carboxylic acids derivatives integrated piperazine-amino acid complexes for α-glucosidase inhibition in vitro
Huang, Jinxiang,Zang, Xufeng,Yang, Wuying,Yin, Xiaoli,Huang, Jianping,Wu, Shumin,Hong, Yanping
, (2021/08/03)
Eighteen derivatives of pentacyclic triterpene carboxylic acids (Maslinic acid, Corosolic acid and Asiatic acid) have been prepared by coupling the piperazine complex of L-amino acids at the C-28 site of the parent compounds. The α-glucosidase inhibitory
2-O-(2-chlorobenzoyl) maslinic acid triggers apoptosis in A2780 human ovarian carcinoma cells
Serbian, Immo,Siewert, Bianka,Al-Harrasi,Csuk, René
, p. 457 - 464 (2019/07/31)
Depending on the conditions of the reactions, maslinic acid can be converted into the corresponding 2-O-, 3-O-, or 2,3-di-O-acylated compounds in good yields. These compounds showed in SRB assays a significantly increased cytotoxicity as compared to the p
