Metabolites Secreted by Bovine Embryos In Vitro Predict Pregnancies That the Recipient Plasma Metabolome Cannot, and Vice Versa

This work describes the use of mass spectrometry-based metabolomics as a non-invasive approach to accurately predict birth prior to embryo transfer (ET) starting from embryo culture media and plasma recipient. Metabolomics was used here as a predictive platform. Day-6 in vitro produced embryos developed singly in modified synthetic oviduct fluid culture medium (CM) drops for 24 h were vitrified as Day-7 blastocysts and transferred to recipients. Day-0 and Day-7 recipient plasma (N = 36 × 2) and CM (N = 36) were analyzed by gas chromatography coupled to the quadrupole time of flight mass spectrometry (GC-qTOF). Metabolites quantified in CM and plasma were analyzed as a function to predict pregnancy at Day-40, Day-62, and birth (univariate and multivariate statistics). Subsequently, a Boolean matrix (F1 score) was constructed with metabolite pairs (one from the embryo, and one from the recipient) to combine the predictive power of embryos and recipients. Validation was performed in independent cohorts of ETs analyzed. Embryos that did not reach birth released more stearic acid, capric acid, palmitic acid, and glyceryl monostearate in CM (i.e., (p < 0.05, FDR < 0.05, Receiver Operator Characteristic—area under curve (ROC-AUC)> 0.669). Within Holstein recipients, hydrocinnamic acid, alanine, and lysine predicted birth (ROC-AUC > 0.778). Asturiana de los Valles recipients that reached birth showed lower concentrations of 6-methyl-5-hepten-2-one, stearic acid, palmitic acid, and hippuric acid (ROC-AUC > 0.832). Embryonal capric acid and glyceryl-monostearate formed F1 scores generally >0.900, with metabolites found both to differ (e.g., hippuric acid, hydrocinnamic acid) or not (e.g., heptadecanoic acid, citric acid) with pregnancy in plasmas, as hypothesized. Efficient lipid metabolism in the embryo and the recipient can allow pregnancy to proceed. Changes in phenolics from plasma suggest that microbiota and liver metabolism influence the pregnancy establishment in cattle.

Synthesis and Performances of Hydrocinnamic Acid Derivatives Containing Alkyl Dihydrazide

In this work, four hydrocinnamic acid derivatives including N, N’-succinic bis(hydrocinnamic acid) dihydrazide (HASUD), N, N’-adipic bis(hydrocinnamic acid) dihydrazide (HAADD), N, N’-sebacic bis(hydrocinnamic acid) dihydrazide (HASED) and N, N’-dodecanedioic bis(hydrocinnamic acid) dihydrazide (HADOD) were synthesized via two liquid reactions. And then fourier transform infrared spectrometer and 1H nuclear magnetic resonance were used to characterize molecular structures of four hydrocinnamic acid derivatives. Additionally, the orthogonal experiment obtained the optimum synthesis process of four hydrocinnamic acid derivatives, and the maximum yield of HASUD, HAADD, HASED and HADOD were 33.3%, 43.2%, 43.5% and 51.9%, respectively. DMol3 was used to optimize geometric structure and obtain frontier orbital energy. Finally, hydrocinnamic acid derivatives and poly(L-lactide) (PLLA) were blended using the torque rheometer to investigate these role in PLLA resin. The resultant from the melt-crystallization process showed that hydrocinnamic acid derivatives as heterogeneous nucleating agents could significantly enhance PLLA’s crystallization.

N, N’-sebacic bis(hydrocinnamic acid) dihydrazide: A crystallization accelerator for poly(L-lactic acid)

Developing more organic nucleating agent with different molecular structure is very instructive to improve the crystallization of poly(L-lactic acid) (PLLA) and explore the crystallization mechanism. In this study, N, N’-sebacic bis(hydrocinnamic acid) dihydrazide (HAD) was synthesized to serve as a nucleating agent for PLLA. The effects of HAD on the non-isothermal crystallization, melting behavior, thermal stability and optical performance of PLLA were investigated by differential scanning calorimeter (DSC), thermogravimetric analysis (TGA), and light transmittance meter. The melt crystallization behavior showed that HAD was able to promote the crystallization of PLLA via heterogenous nucleation in cooling, and it was found that, upon the cooling of 1°C/min, the incorporation of 1 wt% HAD made the crystallization temperature and non-isothermal crystallization enthalpy increase from 94.5°C and 0.1 J/g to 131.6°C and 48.5 J/g comparing with the pure PLLA. Additionally, the melt crystallization significantly depended on the cooling rate and the final melting temperature. For the cold crystallization, when the nucleation density from HAD and PLLA itself was saturated, the influence of the HAD concentration on the cold crystallization process of the PLLA/HAD samples is negligible. The melting behavior after isothermal or non-isothermal crystallization further confirmed the crystallization accelerating effect of HAD for PLLA, and the appearance of the double melting peaks was attributed to the melting-recrystallization. Unfortunately, the addition of HAD decreased the thermal stability and light transmittance of PLLA.

Differentiation and Functionalization of Adjacent, Remote C–H Bonds

<p>Site-selective functionalizations of C–H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures^1-4. Towards this goal, developing strategies to activate C–H bonds that are distal from a functional group is essential^4-6. In this context, distinguishing remote C–H bonds on adjacent carbon atoms is an extraordinary challenge due to the lack of electronic or steric bias between the two positions. Herein, we report the design of a catalytic system leveraging a remote directing template and a transient norbornene mediator to selectively activate a previously inaccessible remote C–H bond that is one bond further away. The generality of this approach has been demonstrated with a range of heterocycles, including a complex anti-leukemia agent, and hydrocinnamic acid substrates.</p>

Differentiation and Functionalization of Adjacent, Remote C–H Bonds

<p>Site-selective functionalizations of C–H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures^1-4. Towards this goal, developing strategies to activate C–H bonds that are distal from a functional group is essential^4-6. In this context, distinguishing remote C–H bonds on adjacent carbon atoms is an extraordinary challenge due to the lack of electronic or steric bias between the two positions. Herein, we report the design of a catalytic system leveraging a remote directing template and a transient norbornene mediator to selectively activate a previously inaccessible remote C–H bond that is one bond further away. The generality of this approach has been demonstrated with a range of heterocycles, including a complex anti-leukemia agent, and hydrocinnamic acid substrates.</p>

Hydrocinnamic acid produced by Enterobacter xiangfangensis impairs AHL-based quorum sensing and biofilm formation in Pseudomonas aeruginosa

Hydrocinnamic acid interacts with LasR receptor averts the autoinducer biding to modulate the expression of quorum sensing mediated phenotypes that strengthens the speculation of hydrocinnamic acid acts as a competitive inhibitor for autoinducer molecule.

Comparison between different liquid-liquid and solid phase methods of extraction prior to the identification of the phenolic fraction present in olive oil washing wastewater from the two-phase olive oil extraction system

Phenolic compounds from olive mill wastewater (OMW), are characterized by a strong antioxidant activity. At the same time, they represent an environmental problem because they are difficult to degrade. The purpose of this work was to identify these biologically active compounds in the OMW from two-phase olive oil production in order to convert a polluting residue into a source of natural antioxidants. After optimizing the extraction process of phenolic compounds using liquid-liquid extraction (LLE) and solid phase extraction (SPE) methods, it was determined that the most appropriate sequence comprised a previous centrifugation to remove the lipid fraction, followed by liquid extraction with ethyl acetate or SPE. The most important compounds identified in olive oil washing wastewater (OOWW) were tyrosol, hydroxytyrosol and succinic acid; whereas the ones in the wastewater derived from the washing of the olives (OWW) were cresol, catechol, 4-methylcatechol, hydrocinnamic acid and p-hydroxy-hydrocinnamic acid.