Large scale production of antitumor cucurbitacins from Ecballium Elaterium using bioreactor

Bioreactor plays a vital role in the commercial production of secondary metabolites and pharmaceuticals from plant cells. Many physical factors, like the mixing intensity, shear stress and operation conditions were optimized as a first step in scaling up process. Qualitative and quantitative determination of cucurbitacins E and I in the extract were carried out using high-performance liquid chromatography (HPLC). After two weeks of equipping the reactor with marine impeller, both the growth rate and the concentration of cucurbitacins were increased. However, the increase in the aeration rate from 0.3 to 0.6 vvm induced the production of cucurbitacin E, it reduced the cucurbitacin I production. The highest recorded level of cucurbitacins was 0.3 and 0.1 g/L for cucurbitacin E and cucurbitacin I, respectively. Crude cucurbitacins extract showed potent antitumor activity in a range of 15.6 to 23.5 μg/ml against various carcinoma cell lines. In the current study, the optimizing condition for the production of cucubitacins E and I in Ecballium Elaterium and their biological activities as an antitumor and antimicrobial agent were evaluated.Keywords: Ecballium Elaterium, cucubitacins E, cucubitacins I, bioreactor, antitumo

Transmission of substituent effects via 1,2,4-triazole ring residue

1012-1016The ionization constants of a series of 5-phenyl-3-substituted phenyl-1,2,4-triazole- 3-carboxylic acids (2a-j), prepared by the base catalysed rearrangement of 2-phenyl-4-arylazo-5-oxazolones (1a-j), and the rate of alkaline hydrolysis of the corresponding methyl esters (3a-j) have been measured in 80% (v/v) ethanol at 30°C and ionic strength of 0.1. Both the equilibrium and rate constants have been correlated by Hammett equation, the values of the reaction constant p being 0.45 and 0.24 respectively. A comparison of presently reported values with those reported in literature for ionization of benzoic acids and alkaline hydrolysis of methyl benzoates indicates that the 1,3-(1,3,4-triazole) ring residue is 39% and 10% efficient in transmitting substituent electronic effects in 2 and 3 respectively

Facile Synthesis, Biological Evaluation, DFT Studies and <i>in Silico</i> Prediction ADME/Pharmacokinetics Properties of <i>N</i>-(1-(2-Chlorobenzo[h]Quinolin-3-yl)-1-Substituted-vin-2-yl)Benzamide Derivatives

A new series of various N-(1-(2-chlorobenzo[h]quinolin-3-yl)-1-substituted-vin-2-yl)benzamide derivatives was designed and synthesized based on the 2-chlorobenzo[h]quinoline core as potential antioxidant and insecticidal agents. In vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidant (ascorbic acid). The results showed good antioxidant activities of these compounds. In addition, in vitro insecticidal activities revealed that most of these compounds exhibited high insecticidal activity against cotton leafworm compared with chlorpyrifos. Some compounds in these series were better than the commercial insecticidal, chlorpyrifos.</p

Polarity and steric effect of di-lateral substitution on the mesophase behaviour of some azo/ester compounds

<p>Eight homologous series of 2-(or 3-)substituted phenyl 4ʹ-(4″-alkoxy (2ʹ-, or 3″-substituted phenylazo) benzoates (<b>I</b><i>n</i>_XY) were prepared in which the suffix ‘X’ refers to the lateral substituent X attached to the terminal benzene ring that carries the alkoxy group, and the suffix ‘Y’ refers to the substituent attached to the other terminal phenyl group. Within each homologous series, the length of the terminal alkoxy group varies from 8 to 16 carbons, while the lateral polar substituents, X and Y, alternatively varies between CH₃ and F. The mesophase behaviour was investigated by differential scanning calorimetry and identified by polarised optical microscopy. The results were discussed in terms of the polarity and steric effects of the two lateral substituents. Comparative correlations were made to investigate the effect of the second lateral substituent on the mesophase behaviour of the previously investigated mono-laterally substituted analogues. UV–vis spectroscopic study revealed that the compounds <b>I</b><i>8</i>_XY exhibited two absorption bands: low intense bands at 254–263 and a broad band at 364–376 nm. These bands are attributed to the π–π∗ transition of the phenyl rings and the whole mesogenic portion.</p

Effect of including extra phenylazo moiety on the mesophase behaviour of three-ring azo/ester molecules

<p>Five homologous series of the four-ring 4-substituted phenylazo phenyl 4ʹ-(4ʹ-alkoxy phenylazo) benzoates (<b>I</b><i>n</i>_a–e) were prepared and their mesophase behaviour investigated by differential scanning calorimetry (DSC) and phases identified by polarised light microscopy (PLM). Compounds prepared were structurally characterised via infrared, ¹H-NMR, mass spectroscopy, thermogravimetric and elemental analysis. Transition temperatures were first correlated with the alkoxy-chain length (<i>n</i>, that varies between 6, 8, 10, 14, and 16 carbons) within each homologous series, and again with the polarisability anisotropy (Δα_X) of the Ar-X bond, where X changes between CH₃O, CH₃, H, Br, and CN groups . Comparative studies were made to investigate the effect of introducing the extra phenyl azo moiety into the previously investigated three-ring compounds, 4-substituted phenyl 4′-(4″-alkoxyphenylazo) benzoates (<b>II</b><i>n</i>_a–e), 4-substituted phenylazo 4′-(4″- alkoxy phenyl) benzoates (<b>III</b><i>n</i>_a–e), and 4-(4′-alkoxy phenylazo) phenyl 4″-substituted benzoates (<b>IV</b><i>n</i>_a–e), each bear the same polar group, X, and the alkoxy group, <i>n</i> .</p

Effect of exchange of terminal substituents on the mesophase behaviour of some azo/ester compounds

<div><p>Six homologous series of 4-(4′-alkoxy phenylazo) phenyl 4″-substituted benzoates (<b>I</b><i>n</i>_a-f) were prepared in which, within each homologous series, the length of the terminal alkoxy chain varies between 6, 8, 10, and 12 carbons, while the other terminal substituent, X, is a polar group that alternatively changed from CH₃O, CH₃, H, Br, NO₂ and CN. Compounds prepared were characterised by spectroscopic methods, and their mesophase behaviour investigated by differential scanning calorimetry (DSC) and polarised optical microscopy (POM). The results were discussed in terms of mesomeric and polarisability effects. In each group of compounds, bearing the same alkoxy substituent, the nematic-to-isotropic transition temperatures (<i>T</i>_C) were successfully correlated with the polarisability anisotropy of bonds to the substituent X. A comparative study was made between the investigated compounds and their previously prepared isomers, namely, 4-(4′-substituted phenylazo) phenyl 4″-alkoxybenzoates (<b>II</b><i>n</i>_a-f) in which the two terminal (alkoxy- and X) groups are exchanged.</p></div

The effect of inversion of the ester group on the mesophase behaviour of some azo/ester compounds

<div><p>Five homologous series of 4-substituted phenyl 4′-(4″-alkoxy phenylazo) benzoates (<b>I</b><i>n</i>_a_–_−e) were prepared in which, within each homologous series, the length of the terminal alkoxy group varies between 8, 10, 12, 14 and 16 carbons, while the other terminal substituent, X, is a polar group that alternatively changed from CH₃O, CH₃, H, Br, and CN groups. Compounds prepared were characterised by infrared, mass, and H¹-NMR spectroscopy and their mesophase behaviour investigated by differential scanning calorimetry (DSC) and polarised light microscopy (PLM). The results were discussed in terms of mesomeric and polarisability effects. Only for the lower group of compounds, <b>I</b>8_a-e, that showed a nematic phase, the nematic-to-isotropic transition temperatures (<i>T</i>_N–I) were successfully correlated to the polarisability anisotropy of bonds to the substituent X. A comparative study was made between the investigated compounds and two previously prepared isomeric groups. In the first group of isomers, 4-(4′alkoxy phenylazo) phenyl 4″-substituted benzoates (<b>II</b><i>n</i>_a_–_e), the ester groups are inverted. While in the second, 4-(4′-substituted phenylazo) phenyl 4″-alkoxy benzoates (<b>III</b><i>n</i>_a_–_e), two modifications were made, inversion of the COO group, and exchange of the two wing substituents</p></div

The effect of orientation of the lateral methyl substituent on the mesophase behaviour of 4-alkoxyphenylazo aryl benzoates

<p>Two homologous series of 4-alkoxyphenylazo 4ʹ-(2ʺ- (and 3ʺ-) methyl-) 4ʹ-substituted benzoates (<b>II</b><i>n</i>_a–f and <b>III</b><i>n</i>_a–f, six series each) were prepared and investigated. Within each series, the length of the terminal alkoxy group varies among 6, 8, 10 and 12 carbons, while the other terminal substituent, X, is a polar group that alternatively changes between the electron-donating CH₃O, CH₃, and the electron-withdrawing Br, NO₂ and CN groups, in addition to the un-substituted analogue, X = H, aiming to investigate the effect of the different orientations of the methyl groups substituted on the central benzene ring, on the mesophase behaviour. The mesomorphic properties were discussed in terms of steric and polarisability effects. The mesophase stability was correlated with the polarisability anisotropy of bonds to the terminal substituent X. Comparative studies were made between the prepared isomers with each other and with the previously investigated laterally neat analogues 4-(4ʹ-alkoxyphenylazo) phenyl 4ʺ-substituted benzoates (<b>I</b><i>n</i>_a–f).</p