Proton Nuclear Magnetic Resonance-Based Method for the Quantification of Epoxidized Methyl Oleate

Epoxidized methyl esters (EMO) with their high oxirane ring reactivity, acts as a raw material in the synthesis of various industrial chemicals including polymers, stabilizers, plasticizers, glycols, polyols, carbonyl compounds, biolubricants etc. EMO has been generally quantified by the gas chromatography (GC) and high-performance liquid chromatography (HPLC) techniques. Taking into the account of the limitations of these techniques, two qHNMR-based equations have been proposed for the quantification of EMO in the mixture of EMO and methylesters (MO). The validity of the proposed method was determined using standard mixtures of MO and EMO having different molar concentrations. The developed equations have been applied on the samples of EMO prepared from oleic acid in two-step process viz., esterification followed by epoxidation. The qHNMR-based EMO quantification showed acceptable agreement with the results obtained from HPLC analysis.     

Identification and Composition of Clasper Scent Gland Components of the Butterfly Heliconius erato and Its Relation to Mimicry

The butterfly Heliconius erato occurs in various mimetic morphs. The male clasper scent gland releases an anti-aphrodisiac pheromone and additionally contains a complex mixture of up to 350 components, varying between individuals. In 114 samples of five different mimicry groups and their hybrids 750 different compounds were detected by gas chromatography/mass spectrometry (GC/MS). Many unknown components occurred, which were identified using their mass spectra, gas chromatography/infrared spectroscopy (GC/IR)-analyses, derivatization, and synthesis. Key compounds proved to be various esters of 3-oxohexan-1-ol and (Z)-3-hexen-1-ol with (S)-2,3-dihydrofarnesoic acid, accompanied by a large variety of other esters with longer terpene acids, fatty acids, and various alcohols. In addition, linear terpenes with up to seven uniformly connected isoprene units occur, e. g. farnesylfarnesol. A large number of the compounds have not been reported before from nature. Discriminant analyses of principal components of the gland contents showed that the iridescent mimicry group differs strongly from the other, mostly also separated, mimicry groups. Comparison with data from other species indicated that Heliconius recruits different biosynthetic pathways in a species-specific manner for semiochemical formation.     

Distributions of Polycyclic Aromatic Hydrocarbons and Phthalic Acid Esters in Gums and Soapstocks Obtained from Soybean Oil Refinery

Soybean oil gums and soapstocks are important by-products that may potentially be contaminated by persistent organic pollutants (POP) such as polycyclic aromatic hydrocarbons (PAH) and phthalic acid esters (PAE), thus lowering the value when using them as starting materials to produce animal feed additives, food industry ingredients, and pharmaceutical products. In the present work, PAH and PAE distributions in these two types of by-products were detected using solvent extraction–solid phase extraction purification coupled with gas chromatography–mass spectrometry. Total PAH and PAE amounts in the soapstocks were significantly higher than those in the gums, thus indicating that neutralization showed much higher removal efficiency than degumming in terms of PAH and PAE eliminations. Meanwhile, the results proved that the concentrations of these two kinds of contaminants in the soybean oil gums and soapstocks were much higher than those in the soybean oils, suggesting that further investigations were needed and that the contents of PAH and PAE in soybean oil refining by-products should be carefully monitored and regulated.     

Structure−Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents

Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.     

Antioxidant effects of gallic acid alkyl esters of various chain lengths in oyster during frying process

The antioxidant effects of gallic acid (GA) and its alkyl esters including methyl gallate, ethyl gallate, propyl gallate, butyl gallate (GA-C4), octyl gallate, lauryl gallate, hexadecyl gallate and octadecyl gallate in frying oil (soybean oil) and oyster during frying were investigated. Rancimat induction period (RIP) assay indicated GA and its alkyl esters effectively improved the oxidative stability of soybean oil according to the ‘polar paradox’; that is, the antioxidant effects of the polyphenols decreased in lipid system with the increasing of hydrophobicity. Results also indicated that GA and its alkyl esters all effectively retarded lipid oxidation in oyster tissue according to parameters including RIP, peroxide value and electron spin resonance assays. Moreover, the antioxidant efficiency in oyster increased with the alkyl chain length until GA-C4, and thereafter, the antioxidant effects decreased, similar to the ‘cut-off effect’. This study provides basic data for improving the oxidative stability of seafood during frying.