1,2,3,4,5,6-hexahydro-α,1,5,5-tetramethyl-γ-oxo-3a,6-Ethano-3aH-indene-4-pentanoic acid

Aims and objective: Condensation of 5-hetarylidene-2,2-dimethyl-1,3-dioxane-4,6- diones with 5,5-dimethyl-3-arylamino-2-cyclohexanones yields 1-aryl-4-hetaryl-7,7-dimethyl-2,5- dioxo-l,2,3,4,5,5,7,8-octahydro-quinolines. The structures of all the synthesized compounds have been verified by IR, 1H-NMR, 13C-NMR, and mass spectral methods. The 13C-NMR assignments were supported by HSQC and HMBC experiments. Moreover, spin decoupling and NOE experiments have been carried out in order to elucidate stereoisomeric configurations of the compounds. It has been established that the N-phenyl ring, which projects from the plane of the octahydroquinolinedione ring, has a shielding effect on the magnetic field of the protons at 7- and 8-positions of the ring in the molecules of the compounds synthesized. Materials and methods: The NMR spectra were recorded on a Varian Gemini spectrometer [400 MHz (1H) and 100 MHz (13C)]. EI mass spectra were obtained with a Hewlett Packard GC/MS 6890/5973 machine. MALDI-TOF mass measurements were recorded on a Bruker auto-flex III smart beam. Results: Various reaction conditions were applied in order to find an optimum and convenient procedure for the formation of octahydroquinoline derivates having hetaryl group. The highest yields (40-50 %) were achieved using acetic acid as solvent, p-toluenesulphonic acid as acidic catalyst, and excess enaminone (1.5 equiv). Conclusion: We synthesized eight new 1-aryl-7,7-dimethyl-4-hetaryl-1,2,3,4,5,6,7,8-octahydroquinoline- 2,5-dione compounds containing thienyl core as a result of Michael addition reaction of Knoevenagel products of Meldrum's acid with dimedone enaminone compounds. Optimum circumstances were established using various reaction conditions and catalyzers throughout the research. The structures of all the synthesized compounds were analyzed by IR, 1H-NMR, 13CNMR, and mass spectral methods. Furthermore, the structures were verified with the help of 2D (HSQC and HMBC), spin decoupling, and NOE NMR techniques.

This study evaluated the inhibitory effect of phytic acid (PA) on the spore germination and vegetative cells growth of Clostridium perfringens type A, as well as its effect in combination with maltodextrin (MD) in cooked sausages. The addition of 1% PA showed a satisfactory inhibition of spores' germination and vegetative cells growth of C. perfringens in BHI media. The inhibitory effect of 1% PA on vegetative cells was similar to the additive sodium sorbate (SS) at 10%. Subsequently, a mixture of PA-MD (1:1; w/w) was evaluated for the inhibition of C. perfringens spores in cooked sausages. The PA-MD 1.5% and 2.5% had a similar performance to SS 10% and a similar or higher performance than 0.015% NO2 (p < 0.05). In an unprecedented way, the present study demonstrated that PA inhibited spore germination and vegetative cells growth of C. perfringens, highlighting its potential use as an alternative and natural preservative for the meat industry.

β-Carbolines are naturally occurring bioactive alkaloids. In this work, carbohydrate-derived β-carbolines (βCs), 1-(1,3,4,5-tetrahydroxypent-1-yl)-β-carboline isomers (1a/b), 1-(1,4,5-trihydroxypent-1-yl)-β-carboline (2), 1-(1,5-dihydroxypent-3-en-1-yl)-β-carboline (3), and 1-(1,2,3,4,5-pentahydroxypent-1-yl)-β-carboline (4) were identified and analyzed in commercial foods. The concentrations of βCs 1-4 in foods ranged from undetectable to 11.4 μg/g levels, suggesting their intake in the diet. Processed foods contained higher amounts than fresh or unprocessed foods, and the highest content was found in processed tomato and fruit products, sauces, and baked foods. βCs 1-3 were formed in foods during heating, and 1a/b were the main compounds. The formation of carbohydrate-derived βCs was studied in model reactions of tryptophan and carbohydrates. They formed in reactions of tryptophan with glucose under acidic conditions at temperatures higher than 80 °C. The formation of 1a/b was favored, but 2-3 increased at high temperatures. Noticeably, the βCs 1-3 formed in the reactions of tryptophan with fructose or sucrose, and the formation from fructose was much higher than from glucose. Thus, fructose was the main carbohydrate involved in the formation of 1-3, whereas sucrose gave these βCs after acid hydrolysis. It is shown for the first time that the mechanism of formation of βCs 1-3 occurs from the sugar intermediate 3-deoxyglucosone that reacts with tryptophan affording these carbohydrate-derived βCs. A mechanism of reaction to give βCs 1-3 is proposed that relies on the tautomerism (keto-enediol or enamine-imine) of intermediates involved in the reaction. Carbohydrate βCs 1-4 were assessed as inhibitors of monoamine oxidase (MAO), as antioxidants, and for their interaction with DNA. They were not good inhibitors of MAO-A or -B, were poor antioxidants, and did not appreciably interact with DNA.