Hong-Juan Li

Synthesis, antitumor activity evaluation of some new N -aroyl- α , β -unsaturated piperidones with fluorescence

Abstract Novel N-aroyl-α,β-unsaturated piperidones, series 1, series 2 and series 3 (featuring 2-bromo-4,5-dimethoxybenzylidene, 4-dimethylaminobenzylidene and 4-trifluoromethylbenzylidene, respectively), were synthesized as candidate cytotoxins. Most of the compounds displayed potent cytotoxicity against the human neoplastic cell lines SK-BR-3, PG-BE1, NCI-H460, MIA PaCa-2 and SW1990 in vitro, and approximately 64% of the IC50 values were lower than 5 μM. Among those tested, compound 1b of series 1, 3a, 3d and 3e of series 3 proved to be the most active. Importantly, 1b displayed marked inhibitory effects on tumor growth in vivo and had no apparent toxicity to mice; this was evaluated by a nude mouse PG-BE1 xenograft model. In addition, the fluorescent properties of compounds series 1–3 were investigated. The interesting fluorescence exhibited by these compounds could be useful for their visualization in tumor cells, permitting further studies on these α,β-unsaturated piperidones as candidates for novel fluorescent antitumor agents.

New sesquiterpenes from the rhizomes of homalomena occulta.

Six new sesquiterpenes (1-6), along with eight known ones (7-14) were isolated from the rhizomes of Homalomena occulta. Structure elucidation of the new compounds was achieved through 1D NMR, 2D NMR spectroscopic techniques and HRESIMS, while the absolute configurations of compounds 1, 2 and 5 were confirmed by X-ray crystallographic analysis. All of the isolates were evaluated for their activity against LPS-induced production of nitrogen oxide (NO) in macrophage cells, and compounds 1 and 5 showed inhibitory effect on NO production with the IC50 values of 21.2 and 15.4 μM, respectively.

Synthesis, Antiproliferative, and Multidrug Resistance Reversal Activities of Heterocyclic α,β-Unsaturated Carbonyl Compounds.

A series of heterocyclic α,β‐unsaturated carbonyl compounds (1a‐1d, 2a‐2d, 3a‐3d, 4a‐3d, and 5a‐5d) with 1,5‐diaryl‐3‐oxo‐1,4‐pentadienyl pharmacophore were synthesized for the development of anticancer and multidrug resistance reverting agents. The antiproliferative activities were tested against nine human cancer cell lines. Approximately 73% of the IC50 values were below 5 μm, while 35% of these figures were submicromolar, and compounds 3a‐3d with 4‐trifluoro methyl in the arylidene benzene rings were the most potent, since their IC50 values are between 0.06 and 3.09 μm against all cancer cell lines employed. Meanwhile, their multidrug resistance reversal properties and cellular uptake were further examined. The data displayed that all of these compounds could reverse multidrug resistance, particularly, compounds 3a and 4a demonstrated both potent multidrug resistance reverting properties and strong antiproliferative activities, which can be taken as leading molecules for further research of dual effect agents in tumor chemotherapy.

Quaternary ammonium salts substituted by 5-phenyl-1,3,4-oxadiazole-2-thiol as novel antibacterial agents with low cytotoxicity

Twenty‐one novel 5‐phenyl‐1,3,4‐oxadiazole‐2‐thiol (POT) substituted N‐hydroxyethyl quaternary ammonium salts (6a–g, 7a–g, 8a–g) were prepared and characterized by FTIR, NMR, and elemental analysis. Compounds 6a, 6c, and 8a were confirmed by X‐ray single‐crystal diffraction. They display the unsurpassed antibacterial activity against Staphylococcus aureus, α‐H‐tococcus, Escherichia coli, P. aeruginosa, Proteus vulgaris, Canidia Albicans, especially 6g, 7g, 8g with dodecyl group. Compounds 8a–d with N,N‐dihydroxyethyl and POT groups display unsurpassed antibacterial activity and non‐toxicity. The structure–activity relationships indicate that POT and flexible dihydroxyethyl group in QAS are necessary for antibacterial activity and cytotoxicity. SEM and TEM images of E. coli morphologies of 8d show the antibacterial agents can adhere to membrane surfaces to inhibit bacterial growth by disrupting peptidoglycan formation and releasing bacterial cytoplasm from cell membranes.

Preparative separation of phloridzin from apple leaves using macroporous resins followed by preparative high-performance liquid chromatography

Phloridzin is one of the major phenolic compounds in apple and has been widely used in medicine for a long time due to its significant biomedical activities. In this article, macroporous resin was used for purification of phloridzin from apple leaves. The HPD-300 resin was selected for the enrichement of phloridzin according to its high adsorption and desorption capacities. The adsorption kinetics and isotherms were constructed on the HPD-300 resin and fitted well to the pseudo-second-order kinetic model and Langmuir model, respectively. Dynamic adsorption and desorption tests were performed on the column packed with HPD-300 resin to optimize the operating parameters. After one round treatment with HPD-300 resin, the purity of phloridzin in the product increased from 11.4 to 50.1% with a recovery yield of 79.3%. Subsequently, preparative high-performance liquid chromatography was employed for the purification of phloridzin. The purity of phloridzin could reach above 98% after further recrystallization with a recovery yield of 75.8%.

Synthesis, physiochemical property and antimicrobial activity of novel quaternary ammonium salts

Abstract Twenty-four novel 5-phenyl-1,3,4-oxadiazole-2-thiol (POT) analogues, benzo[d]oxazole-2-thiol, benzo[d]thiazole-2-thiol and 5-methyl-1,3,4-thiadiazole-2-thiol-substituted N,N-bis(2-hydroxyethyl) quaternary ammonium salts (QAS) (5a-d, 6a-d, 7a-d, 10a-d, 13a-d, 16a-d) were prepared and characterised by FTIR, NMR and elemental analysis. Part of target compounds (5d, 6d, 7d, 10d, 13d, 16d) displayed potent antimicrobial effect against ten common pathogens (S. aureus, α-H-tococcus, β-H-tococcus, E. coli, P. aeruginosa, Proteus vulgaris, Canidia Albicans, Cytospora mandshurica, Physalospora piricola, Aspergillus niger) and had relatively low cytotoxity against two human cell lines (HaCat and LO2). TEM and SEM images of E. coli and S. aureus morphologies treated with 7d showed that the antibacterial mechanism might be the QAS fixing on cell wall surfaces and puncturing to result in the release of bacterial cytoplasm. This study provides new information of QAS, which could be used to design novel antimicrobial agents applied in clinic or agriculture. Graphical Abstract