Different types of enzymes such as lipases, several phosphatases, dehydrogenases, oxidases, amylases and others are well suited for the reactions in SC-CO2. The stability and the activity of enzymes exposed to carbon dioxide under high pressure depend on enzyme species, water content in the solution and on the pressure and temperature of the reaction system. The three-dimensional structure of enzymes may be significantly altered under extreme conditions, causing their denaturation and consequent loss of activity. If the conditions are less adverse, the protein structure may be largely retained. Minor structural changes may induce an alternative active protein state with altered enzyme activity, specificity and stability.

Natural and abundant plant triterpenoids are attractive starting materials for the synthesis of conformationally rigid and chiral building blocks for functional soft materials. Here, we report the rational design of three oleanolic acid–triazole–spermine conjugates, containing either one or two spermine units in the target molecules, using the Cu­(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The resulting amphiphile-like molecules 2 and 3, bearing just one spermine unit in the respective molecules, self-assemble into highly entangled fibrous networks leading to gelation at a concentration as low as 0.5% in alcoholic solvents. Using step-strain rheological measurements, we show rapid self-recovery (up to 96% of the initial storage modulus) and sol ⇔ gel transition under several cycles. Interestingly, rheological flow curves reveal the thixotropic behavior of the gels. To the best of our knowledge, this kind of behavior was not shown in the literature before, neither for a triterpenoid nor for its derivatives. Conjugate 4, having a bolaamphiphile-like structure, was found to be a nongelator. Our results indicate that the position and number of spermine units alter the gelation properties, gel strength, and their self-assembly behavior. Preliminary cytotoxicity studies of the target compounds 2–4 in four human cancer cell lines suggest that the position and number of spermine units affect the biological activity. Our results also encourage exploring other triterpenoids and their derivatives as sustainable, renewable, and biologically active building blocks for multifunctional soft organic nanomaterials.

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Cytotoxicity data: 8a: IC50 [μM]: 18.8/31.8/32.6/17.2 (25.1 ± 8.2), due to the dynamic self-assembly found, low-contrast networks (TEM); 8b: IC50 [μM]: 7.5 ± 1.6, dynamic self-assembly not detected, partly helical structures (TEM).

Increasing crop productivity is our major challenge if we are to meet global needs for food, feed and fuel. Controlling the level of the plant hormones cytokinins is a mean of improving plant productivity. Cytokinin oxidase/dehydrogenase (CKO/CKX) is a major target in this regard because it degrades cytokinins. Here, we describe the synthesis and biological activities of new CKX inhibitors derived mainly from diphenylurea. They were tested on four CKX isoforms from maize and Arabidopsis, where the best compounds showed IC50 values in the 10 -8 M concentration range. The binding mode of the most efficient inhibitors was characterized from high-resolution crystal complexed structures. Although these compounds do not possess intrinsic cytokinin activity, we have demonstrated their tremendous potential for use in the plant tissue culture industry as well as in agriculture. We have identified a key substance, compound 19, which increases stress resistance and seed yield in Arabidopsis, but also improves the yield of wheat, barley and rapeseed grains under field conditions. Thus our findings reveal that subtle modulation of cytokinin levels via CKX inhibition can positively affect plant growth, development and yield, and underline the fact that CKX inhibitors truly deserve to attract interest in plant biotechnology and agriculture

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Supercritical fluid extraction represents an efficient and environmentally friendly technique for isolation of phytosterols from different plant sources. Sea buckthorn (Hippophae rhamnoides L.) seeds were extracted with supercritical carbon dioxide at pressures ranging from 15–60 MPa and temperatures of 40–80 °C. Oil and β-sitosterol yields were measured in the extraction course and compared with Soxhlet extraction with hexane. The average yield of β-sitosterol was 0.31 mg/g of seeds. The maximum concentration of β-sitosterol in the extract, 0.5% w/w, was achieved at 15 MPa, 40 °C, and a carbon dioxide consumption of 50 g/g of seeds. The extraction rate was maximal at 60 MPa and 40 °C. Both β-sitosterol yield and its concentration in the extract obtained with hexane were lower than with carbon dioxide.