Research progress on classification,source,application of phytosterol esters,and their thermal oxidation stability

Phytosterol esters can effectively decrease serum cholesterol concentration in the human body and prevent cardio-cerebrovascular diseases.It was found that phytosterol esters exhibited better solubility and bioavailability than free phytosterols.In recent years,phytosterol esters have attracted increasing attention.However,during food processing,phytosterol esters are susceptible to degradation at high temperatures,resulting in certain losses and formation of potentially harmful substances for humans.This paper reviews the relevant literatures and updates on the thermal oxidation stability of phytosterol esters in recent years from the following aspects:(i)Sources,physiological activities,and applications of phytosterol esters;(ii)Oxidation mechanism of phytosterol esters;(iii)Effects of phytosterols species,the volume of addition,food matrix,heating temperature and time,and antioxidants on the thermal loss and oxidation stability of phytosterol esters.The research progress on the safety of phytosterol esters is also discussed in detail.Additionally,the prospects for future research are highlighted.

Study on the regulatory effect of liver X receptor in HEK293 cells by six main diterpene esters in Semen Euphorbiae

Background:To study the effects of the main diterpene esters in Euphorbia factor L_(1),L_(2),L_(3),L_(7a),L_(7b)and L_(8)on the transcriptional activity and protein expression of liver X receptor(LXR).Methods:The effect of the main diterpene ester components in Semen Euphorbiae on the viability of HEK293 cells were studied by MTT assay.The LXR-Luc plasmid vector was transfected into HEK293 cells and treated with Euphorbia factor L_(1),L_(2),L_(3),L_(7a),L_(7b)and L_(8)for 24 h.The effect of the main diterpene ester components of Semen Euphorbiae on LXR-Luc luciferase activity was investigated by dual luciferase reporter gene system,and the expression of LXRαprotein was detected by Western Blot.Results:Euphorbia factor L_(1),L_(2),L_(3),L_(7a),L_(7b)and L_(8)could significantly reduce the relative luciferase activity(RLU)of LXRα,and the expression level of LXRαprotein was significantly down-regulated.Conclusion:Euphorbia factor L_(1),L_(2),L_(3),L_(7a),L_(7b)and L_(8)can inhibit the expression of LXR protein level,which may be achieved by inhibiting the transcriptional activity of LXR.

STRUCTURE OF THERMOTROPIC LIQUID CRYSTALLINE VANILLIC ACID/P-HYDROXYBENZOIC ACID/ETHYLENE TEREPHTHALATE VHE TERPOLYESTERS

Thermotropic liquid crystalline VHE terpolyesters made from vanillic acid (V),p-hydroxybenzoic acid (H) and poly(ethylene terephthalate) (E) were studied by 400 MHz NMR spectra, wide angle X-ray diffraction,scanning electron and polarizing microscopes.It was found that the VHE terpolyesters had random sequence distribution.The VHE terpolyester films exhibited highly oriented fibrillar structure.

Pollution characteristics and risk assessment of organophosphate esters in aquaculture farms and natural water bodies adjacent to the Huanghe River delta

To date,little attention has been paid to the effects of organophosphate esters(OPEs)pollution on aquacultural environment and aquatic product safety.Huanghe(Yellow)River delta area is one of the largest aquaculture centers in China,where ecological security protection is crucial in the national strategy of China.To explore the pollution characteristics,bioaccumulation,and health risks of OPEs in aquaculture farms in the Huanghe River delta and natural water bodies in the adjacent seas,five species of organisms from different farm types nearby the Huanghe River delta,and the corresponding culture water and sediments were sampled in this study.The total concentrations of Σ_(13)OPEs in water,sediments,and organisms were 51.53-272.18 ng/L,52.63-63.17 ng/g dry weight(dw),and 46.82-108.90 ng/g dw,respectively.Among the five types of culture ponds,the water samples from the swimming crab and hairy crab culture ponds exhibited higher OPEs,the concentration of OPEs in the sediments from the few ponds was relatively balanced,and the OPEs in the organism from the holothurian ponds was higher.Tris(1,3-dichloro-2-isopropyl pho sphate)(TDCP)was the main contaminant in water samples and tripropyl phosphate(TPrP)in sediments and organisms.However,trisphenyl phosphate(TPhP)showed the strongest bioaccumulation ability,followed by 2-ethylhexyl diphenyl phosphate(EHDPP)and TPrP.The bioaccumulation capacities of the five species were as follows:prawn>holothurian>hairy crab>swimming crab>carp.These five types of organisms,as main seafood in human consumption,were at low risk of negative impacts of pollution.However,the risk from the mixture of organophosphate flame retardants(OPFRs)still requires more attention due to the increasing consumption and production in the world.

Adsorption of Phthalic Acid Esters by Humic Acid and Its Research Progress

Humic acid is rich in highly electronegative oxygen-containing organic functional groups,so it has high reactivity and can adsorb phthalic acid ester(PAEs)in the environment to reduce the risk of environmental pollution from PAEs.In this paper,the extraction,characterization and adsorption models of humic acid were reviewed,and the research status of adsorption of PAEs by humic acid was further summarized.Based on these,the feasibility and observable application prospect of humic acid as a cheap adsorbent were analyzed.

Pathogenic contribution of cholesteryl ester accumulation in the brain to neurodegenerative disorders

Cholesteryl esters(CEs) have been increasingly implicated in neurodegenerative disorders such as Alzheimer's disease(AD).Alois Alzheimer noted three prominent neuropathologic features in his original analysis of the AD brain:senile plaques,neurofibrillary tangles,and lipid granule accumulation.Senile plaques,which are aggregates of amyloid-beta(Aβ),and neurofibrillary tangles,which are aggregates of phosphorylated tau,have been regarded as more consistent characteristics of the AD brain compared with lipid granule accumulation and thus have been studied more intensively(Foley,2010).

Anticancer Activities of Substituted Cinnamic Acid Phenethyl Esters on Human Cancer Cell Lines

Caffeic acid phenethyl ester (CAPE) and sixteen substituted cinnamic acid phenethyl esters were prepared via conventional procedures in order to test their in vitro anticancer activities by either MTT assay or SRB assay on six different human cancer cell lines. The results indicated that in the concentration of 10μmol·L^-1 the lead compmuM CAPE possessed anficancer activities against human HL-60, Bel-7402, and Hela cell lines, and two other compounds possessed potent anticancer activities against Bel-7402 and Hela cell lines.

Short communication Catalytic synthesis of butyric esters with TiSiW_(12)O_(40)/TiO_2

The catalytic activities of TiSiW_(12)O_(40)/TiO_2 in synthesizing ethylester; propyl ester, n-butyl ester; and amyl ester were reported. It was demonstrated thatTiSiW_(12)O_(40)/TiO_2 is an excellent catalyst. Various factors concerned with esterification wereinvestigated. The optimum conditions were found: the mole ratio of alcohol to acid is 1.3:1, themass ratio of catalyst to reactants is 1.5 percent, and the reaction time is 1.0 h. Under theoptimum conditions, the yields are 88.0 percent for ethyl ester, 94.5 percent for propyl ester, 98.6percent for n-butyl ester, 99.1 percent for n-amyl ester, and 96.7 percent for iso-amyl ester,respectively.

Abiotic degradation of four phthalic acid esters in aqueous phase under natural sunlight irradiation

Abiotic degradability of four phthalic acid esters （PAEs） in the aquatic phase was evaluated over a wide pH range 5-9. The PAE solutions in glass test tubes were placed either in the dark and under the natural sunlight irradiation for evaluating the degradation rate via hydrolysis or photolysis plus hydrolysis, respectively, at ambient temperature for 140 d from autumn to winter in Osaka, Japan. The efficiency of abiotic degradation of the PAEs with relatively short alkyl chains, such as butylbenzyl phthalate （BBP） and di-nbutyl phthalate （DBP）, at neutral pH was significantly lower than that in the acidic or alkaline condition. Photolysis was considered to contribute mainly to the total abiotic degradation at all pH. Neither hydrolysis nor photolysis of di-ethylhexyl phthalate （DEHP） proceeded significantly at any pH, especially hydrolysis at neutral pH was negligible. On the other hand, the degradation rate of di- isononyl phthalate （DINP） catalyzed mainly by photolysis was much higher than those of the other PAEs, and was almost completely removed during the experimental period at pH 5 and 9. As a whole, according to the half-life （t1/2） obtained in the experiments, the abiotic degradability of the PAEs was in the sequence： DINP （32-140 d） 〉 DBP （50-360 d）, BBP （58-480 d） 〉 DEHP （390-1600 d） under sunlight irradiation （via photolysis plus hydrolysis）. Although the abiotic degradation rates for BBP, DBP, and DEHP are much lower than the biodegradation rates reported, the photolysis rate for DINP is comparable to its biodegradation rate in the acidic or alkaline condition.

Cloud point extraction coupled with HPLC-UV for the determination of phthalate esters in environmental water samples

A method based on cloud point extraction was developed to determine phthalate esters including di-ethyl-phthalate （DEP）, di- （2-ethylhexyl）-phthalate （DEHP） and di-cyclohexyl-phthalate （DCP） in environmental water samples using high-performance liquid chromatography separation and ultraviolet detection （HPLC-UV）. The non-ionic surfactant Triton X-114 was chosen as extraction solvent. The parameters affecting extraction efficiency, such as concentrations of Triton X-114 and Na2SO4, equilibration temperature, equilibration time and centrifugation time were evaluated and optimized. Under the optimum conditions, the method can achieve preconcentration factors of 35, 88, 111 and detection of limits of 2.0, 3.8, 1.0 ng/ml for DEP, DEHP and DCP in 10-ml water sample, respectively. The proposed method was successfully applied to the determination of trace amount of phathalate esters in effluent water of the wastewater treatment plant and the lixivium of plastic fragments.

Synthesis of insecticidal sucrose esters

Some synthetic sucrose esters （SE） are a relatively new class of insecticidal compounds produced by reacting sugars with fatty acids, which are safe for the environment. Especially, sucrose esters composed of C6-C12 fatty acids have desirable insecticidal properties against many soft-bodied arthropod pests. In our study, sucrose octanoate which has the highest activity against a range of arthropod species was synthesized by a trans-esterification method and proved its insecticidal property. Under the condition of a homogeneous liquid, sucrose octanoate was prepared by reacting ethyl octanoate with sucrose at reduced pressure; the yield was 79.11%. Sucrose octanoate synthesized was identified and its property analyzed by IR, TLC and spectrophotometric analysis. It was shown that the ratio of monoester to polyester in sucrose octanoate was 1.48：1. The insecticidal activity of the synthetic sucrose octanoate was evaluated at a concentration of 4 and 8 mg.mL^-1. The mortality of first-instar larvae ofLymantria dispar from its contact toxicity was 72.5% after 36 hours, the revision insect reduced rate of Aphis glycines reached above 80% at 4 and 8 mg.mL^-1 after being treated for 5 days. Since the SE products are nontoxic to humans and higher animals, fully biodegradable and hydrolyzed to readily metabolizable sucrose and fatty acid, they are not harmful to crops and appear to be good insecticide candidates.

Analysis of Phthalate Esters in Air, Soil and Plants in Plastic Film Greenhouse

The phthalate esters such as DMP, DEP, DBP and DEHP in air, soil and plant samples in plastic film greenhouse were clean up with fine silica gel column and determined with HPLC. It was found that the concentrations of PEs in air and soil samples in plastic film greenhouse are much higher than those of contrast samples. But concentrations of PEs in plants in plastic film greenhouse are not remarkably affected by the pollution of air and soil.

Highly efficient synthesis of β-amino esters via Mannich-type reaction under solvent-free conditions using ZnCl_2 catalyst

β-Amino esters were synthesized via ZnCl2-catalyzed Mannich-type reaction of imines and malonate esters under solvent-free conditions in 6 min. The β-amino ester was converted into the corresponding aspartic acid derivatives.

The setereoselective preparation ofβ-keto esters using baker's yeast in the presence of rice wine koji

By the addition of rice wine koji, enhancement of the reactivity was observed for the baker＇s yeast reduction of β-keto esters into （S）-β-hydroxy esters with high enantiomeric purity （73-98%）.

Selective debenzylation of benzyl esters by silica-supported sodium hydrogen sulphate

A new debenzylation of benzyl esters by silica-supported sodium hydrogen sulfate is described. The debenzylation could be achieved selectively and efficiently in good to excellent yields without affecting sensitive functional groups such as nitro, unsaturated bonds, and ethyl ester.

Iodine-catalyzed Efficient Synthesis of β-Keto Esters from Aldehydes and Ethyl Diazoacetate Under Solvent-free Conditions

An efficient procedure for the synthesis ofβ-keto esters from the reaction of aldehydes and ethyl diazoacetate catalyzed by iodine at room temperature under solvent-free conditions has been described. The catalytic procedure has the advantages of easily available catalyst, mild reaction conditions, high yields, and easy work-up.

Efficient Syntheses of 2-Substituted Benzimidazoles and Benzoxazoles from β-Keto Esters

An efficient synthetic method was developed to synthesize 2-substituted benzimidazoles and benzo- xazoles with β-keto esters as starting materials under mild reaction conditions, during which other functional groups are bearable from reactants to products.

Biodegradability of four phthalic acid esters under anaerobic condition assessed using natural sediment

Biodegradability of di-n-butyl phthalate （DBP）, butylbenzyl phthalate （BBP）, di-ethylhexyl phthalate （DEHP）, and di-isononyl phthalate （DINP） under an anaerobic condition was evaluated using three natural sediment microcosms obtained from ponds in Osaka, which had not been significantly polluted by the chemicals. The degradabilities of the four phthalic acid esters（PAEs） were analyzed by a first-order kinetic model with a lag phase and ranked as DBP〉BBP〉〉DEHP〉DINP. The PAEs with shorter alkyl-chains, DBP and BBP, were degraded with quite short lag phases near to zero and short half-lives of a few days. The PAEs with longer alkyl-chains, DEHP and DINP, were degraded with lag phases of 5-30 d and the quite long half-lives of a couple of hundred days. Although no data was available on the anaerobic biodegradability of D1NP before this study, it was clarified that DINP can be degraded with slow degradation rates. The fact that all the three intact sediments were capable of biodegradation of the PAEs suggests that potential of anaerobic biodegradation of PAEs is widespread in the aquatic environment.

Two new olean-type triterpene fatty esters from Scorzonera mongolica

Two new triterpene fatty esters, 3β-tetradecanoyl moradiol 1 and 3β-dodecanoyl moradiol 2, were isolated from Scorzonera mongolica. Their structures were elucidated as 3β-tetradecanoyloxy-28-hydroxylolean-18-ene and 3β-dodecanoyl-28-hydroxyl-olean-18-ene on the basis of IR, MS, 1D NMR and extensive 2D NMR spectroscopic analyses.

Boosted Biodegradability and Tribological Properties of Mineral Base Oil by Methyl Diethanolamine Fatty Acid Esters

Methyl diethanolamine fatty acid esters, viz. methyl diethanolamine octanoate and methyl diethanolamine oleate,were prepared. Their impacts on the biodegradability and tribological properties of mineral base oil 400 SN were evaluated by a tester for fast evaluating the biodegradability of lubricants and by a four-ball tester, respectively. The results showed that methyl diethanolamine octanoate and methyl diethanolamine oleate both could markedly promote the biodegradation of the oil and improved its tribological properties. The improvement of biodegradability was attributed to the enhanced growth and quantity of microbes by methyl diethanolamine fatty acid esters. The worn surfaces were analyzed by a scanning electron microscope(SEM) equipped with an energy dispersive spectrometer(EDS) and an X-ray photoelectron spectroscope(XPS). The results indicated that the enhancement of friction-reducing and anti-wear properties of the mineral oil was attributed to the formation of complicated boundary lubrication films composed of species such as Fe_2O_3, Fe_3O_4 and organic nitrogen-containing compounds with a structure of –C-N-or R-NH_2.