2,2’‐dihydroxybenzophenones and derivatives have been synthesized directly or by oxidation of their incipiently obtained benzylic alcohols by diverse efficient methods. Oxime and N‐acyl hydrazone derivatives have also been prepared. Their structure profile has been scrutinized by DFT/B3LYP‐6‐311++G** methodology, NMR spectroscopy and dihedral angle grid scan analysis. Energetically favorable conformations pointed to (i) an almost coplanar bifurcated 6‐membered H bridge in ketones, (ii) a single 6‐membered H bridge, accompanied by a 7‐membered H bonding interaction in oximes and (iii) a single 6‐membered H‐bridge in hydrazones. In the latter case, a stable conformation with an additional 9‐membered pseudo ring was also found. Highly deshielded protons in the NMR spectra are in accordance with the theoretically obtained findings on the H‐bonded conformers. Significant anti‐inflammatory activity of the compounds has been found by in vivo tests with their oxime and hydrazone derivatives showing the highest activity, hydrazone 11, in partucular, competing with marketed drugs. In silico docking studies point to the perspective potency of these structures as COX‐1/COX‐2 inhibitors.
Walnuts have an excellent fatty acid profile, beneficial for coronary heart diseases. A diet rich in walnuts has shown to decrease the total and LDL cholesterol levels as well as lipoprotein levels. In this study, the effects of different doses ofγ-irradiation and different packaging conditions on proximate composition and fatty acid profile of walnuts (Juglans regiaL.) were investigated merging data from different spectroscopic techniques. Walnuts moisture, ash, fat, and protein content as well as fatty acid profile were evaluated immediately after irradiation. GC-FID results showed that SFA increased and MUFA and PUFA decreased with the increase of irradiation dose. Moreover, MUFA/SFA and PUFA/SFA ratios decreasedP<0.05compared to control samples. Furthermore, NMR spectroscopy was implemented to examine possible discrimination patterns based on irradiation dose and packaging. This approach revealed the role of PUFA decrease with the parallel increase of irradiation dose while indicating the protective role of vacuum and MAP compared to air packaging. In conclusion, at irradiation doses of up to 5 kGy, the walnuts retained the nutritional benefits of its fatty acids, in particular MUFA and PUFA. Concerning the different types of packaging, greater stability in the nuts was observed using MAP packaging.
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