Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria

After anaerobic incubation of arctiin (1) from the seeds of Arctium lappa with a human fecal suspension, six metabolites were formed, and their structures were identified as (-)-arctigenin (2), (2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3",4"-dimethoxybenzyl)butyrolactone (3), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3",4"-dimethoxybenzyl)butyrolactone (4), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3"-hydroxy-4"-methoxybenzyl)butyrolactone (5), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3",4"-dihydroxybenzyl)butyrolactone (6), and (-)-enterolactone (7) by various spectroscopic means including two dimensional (2D)-NMR, mass spectrometry, and circular dichroism. A possible metabolic pathway was proposed on the basis of their structures and the time course of the transformation. Enterolactones obtained from the biotransformation of arctiin and secoisolariciresinol diglucoside (SDG, from the seeds of Linum usitatissium) by human intestinal bacteria were proved to be enantiomers, with the (-)-(2R,3R) and (+)-(2S,3S) configurations, respectively. Compound 6 showed the most potent proliferative effect on the growth of MCF-7 human breast cancer cells in culture among 1 and six metabolites, while it showed inhibitory activity on estradiol-mediated proliferation of MCF-7 cells at a concentration of 10 microM. These results indicate that the transformation of 1 by intestinal flora might be essential for the manifestation of the estrogenic and antiestrogenic activity of 1.     

Phytochemical Profiling of Lavandula coronopifolia Poir. Aerial Parts Extract and Its Larvicidal,Antibacterial, and Antibiofilm Activity Against Pseudomonas aeruginosa

Infections associated with the emergence of multidrug resistance and mosquito-borne diseases have resulted in serious crises associated with high mortality and left behind a huge socioeconomic burden. The chemical investigation of Lavandula coronopifolia aerial parts extract using HPLC–MS/MS led to the tentative identification of 46 compounds belonging to phenolic acids, flavonoids and their glycosides, and biflavonoids. The extract displayed larvicidal activity against Culex pipiens larvae (LC₅₀ = 29.08 µg/mL at 72 h). It significantly inhibited cytochrome P-450 monooxygenase (CYP450), acetylcholinesterase (AChE), and carboxylesterase (CarE) enzymes with the comparable pattern to the control group, which could explain the mode of larvae toxification. The extract also inhibited the biofilm formation of Pseudomonas aeruginosa by 17–38% at different Minimum Inhibitory Concentrations (MICs) (0.5–0.125 mg/mL) while the activity was doubled when combined with ciprofloxacin (ratio = 1:1 v:v). In conclusion, the wild plant, L. coronopifolia, can be considered a promising natural source against resistant bacteria and infectious carriers.     

Synthesis and reactions of some new selenolo[2,3-<Emphasis Type="Italic">c</Emphasis>]pyridazines

New series of selenolo[2,3-c]pyridazine and pyrimido[4',5':4,5]selenolo[2,3-c]pyridazine derivatives were prepared from 4-cyano-5,6-diphenylpyridazine-3(2H)-selenone. Elemental analysis, IR, ¹H NMR, and mass spectra confirmed the structures of the newly synthesized compounds.     

The reactions of 4-substituted-7-aminothieno-[3,4-d]pyridazines and 2-methyl-6-aminothienopyridine-5-thione with electron-poor olefins and acetylenes

Cycloadditions of thienopyridazines and a thienopyridine with electron-poor olefins and acetylenes as dienophiles are described. The nonisolable adducts undergo subsequent loss of hydrogen sulfide to give substituted phthalazines and substituted isoquinolines, respectively. © 1997 John Wiley & Sons, Inc.     

Enrichment of Zinc and Iron Micronutrients in Lentil (Lens culinaris Medik.) through Biofortification

Biofortification of pulse crops with Zn and Fe is a viable approach to combat their widespread deficiencies in humans. Lentil (Lens culinaris Medik.) is a widely consumed edible crop possessing a high level of Zn and Fe micronutrients. Thus, the present study was conducted to examine the influence of foliar application of Zn and Fe on productivity, concentration, uptake and the economics of lentil cultivation (LL 931). For this, different treatment combinations of ZnSO₄·7H₂O (0.5%) and FeSO₄·7H₂O (0.5%), along with the recommended dose of fertilizer (RDF), were applied to the lentil. The results of study reported that the combined foliar application of ZnSO₄·7H₂O (0.5%) + FeSO₄·7H₂O (0.5%) at pre-flowering (S1) and pod formation (S2) stages was most effective in enhancing grain and straw yield, Zn and Fe concentration, and uptake. However, the outcome of this treatment was statistically on par with the results obtained under the treatment ZnSO₄·7H₂O (0.5%) + FeSO₄·7H₂O (0.5%) at S1 stage. A single spray of ZnSO₄·7H₂O (0.5%) + FeSO₄·7H₂O (0.5%) at S1 stage enhanced the grain and straw yield up to 39.6% and 51.8%, respectively. Similarly, Zn and Fe concentrations showed enhancement in grain (10.9% and 20.4%, respectively) and straw (27.5% and 27.6% respectively) of the lentil. The increase in Zn and Fe uptake by grain was 54.8% and 68.0%, respectively, whereas uptake by straw was 93.6% and 93.7%, respectively. Also the benefit:cost was the highest (1.96) with application of ZnSO₄·7H₂O (0.5%) + FeSO₄·7H₂O (0.5%) at S1 stage. Conclusively, the combined use of ZnSO₄·7H₂O (0.5%) + FeSO₄·7H₂O (0.5%) at S1 stage can contribute significantly towards yield, Zn and Fe concentration, as well as uptake and the economic returns of lentil to remediate the Zn and Fe deficiency.     

Reusable photoresponsive Ag/AgCl nanocube-catalyzed one-pot synthesis of seleno[2,3-b]pyridine derivatives

Research on Chemical Intermediates - In this study, a facile and rapid method was developed to synthesize intensely organoselenium compounds, namely ethylseleno[2,3-b]pyridine carboxylate,...     

Crystal and Molecular Structure of Acylalmino Derivatives of 1-(2,4,6-Trichlorophenyl)-4,5-dihydropyrazol-5-one

The structure of acylamino derivatives of 1-(2,4,6-trichlorophenyl)-4,5-dihydropyrazol-5-one was studied by X-ray diffraction. 3-Acetylamino-1-(2,4,6-trichlorophenyl)-4,5-dihydropyrazol-5-one and 3-benzoylamino-1-(2,4,6-trichlorophenyl)-4,5-dihydropyrazol-5-one exist in crystal as CH tautomers. The nature and number of acylamino groups were found to affect the nature of intermolecular hydrogen bonds in the crystals studied.     

Development and validation of a high-performance thin-layer chromatography densitometric method for the simultaneous determination of novel 1-acridinyl-1,2,3-triazole derivatives

JPC – Journal of Planar Chromatography – Modern TLC - High-performance thin-layer chromatographic (HPTLC) method provides a simple, sensitive, and accurate analytical method for the...     

Phase properties of a Jaynes-Cummings model with Stark shift and Kerr medium

Phase properties of the field interacting with a two-level atom in a lossless cavity Jaynes-Cummings model, taking into account the level shifts produced by Stark effect with an additional Kerr medium for one-mode are studied using the phase formalism of Pegg and Barnett. It is shown in particular that phase properties of the field reflect the collapse and revival phenomena. The results for the time evolution of the phase probability distribution and the phase fluctuations are obtained. The effect of Stark shift on the phase properties in both the absence and presence of a Kerr medium is analyzed. Phase localization is found for certain choice of the parameters. Received: 27 March 1998 / Revised: 8 June 1998 / Accepted: 9 June 1998