Determination of the content of wax esters in some sea foods and their molecular composition. A comparison with ω-3 enriched wax esters

Wax esters enriched in ω-3 fatty acids have been recently shown to be readily absorbed by rats after dietary supplementation. Wax esters are less prone to oxidation and can be better formulated than liquid ω-3 derivatives. All these characteristics suggest a possible use of wax esters enriched in ω-3 as food supplements. However, some naturally occurring wax esters are defined as scarcely digestible (jojoba oil, spermaceti). On the other hand, wax esters have been found in several sources of marine origin, which can enter normal foodstuff. In order to better understand the digestibility of wax esters, we have analysed some foods from marine sources. The content of triglycerides and wax esters of the foods has been determined. Moreover, wax esters have been analysed for their composition in alcohols and fatty acids. Wax esters have been shown to be a part of the neutral lipid extract of the foods analysed. Their content, if compared with the content in triglycerides, shows striking differences. In the case of two botargo preparations, it has been shown that wax esters are more than 90% of the total neutral lipid extract. The content of fatty acids and alcohols found in the foods analysed is consistent with published data.     

Proton nuclear magnetic resonance rapid and structure-specific determination ofω-3 polyunsaturated fatty acids in fish lipids

Based on proton nuclear magnetic resonance (¹H-NMR) spectroscopy, a rapid and structure-specific method for the determination of ω-3 polyunsaturated fatty acids (PUFAs) in fish lipids is presented. The different chemical shift observed for the methyl resonance of ω-3 PUFAs (δ=0.95 ppm) with respect to the methyl resonance of all other fatty acids (δ=0.86 ppm) has provided the possibility of proposing a new and rapid method for the determination of ω-3 PUFA content. Twenty-four fish lipid samples (raw, cooked and canned albacore tuna) produced results that showed good agreement between¹H-NMR analysis and gas chromatographic determination. Raw and cooked samples showed significantly higher levels of ω-3 PUFA than canned tuna.     

Feeding rats with liposomes or fish oil differently affects their lipid metabolism

Two n‐3 polyunsaturated fatty acid (PUFA)‐rich diets differing in their chemical and physical forms were given to rats during 2 wk. Liposomes [phospholipids (PL) organized in bilayer structures] made from a natural marine lipid extract or a mixture of fats containing fish oil [similar fatty acids esterified in triacylglycerols (TAG)] were used. The influence of n‐3 PUFA dietary sources on plasma parameters, i.e. TAG, cholesterol and PL concentrations, was investigated. A similar hypotriglyceridemic effect of n‐3 PUFA from liposomes or fish oil was observed. In contrast, feeding rats with liposomes led to different PL and cholesterol patterns. In the plasma of rats fed liposomes, total cholesterol amounts were positively correlated with PL levels. Liposome and fish oil feedings caused a marked increase in the amounts of n‐3 PUFA, which occurred mainly at the expense of n‐6 PUFA. However, the enrichment in n‐3 PUFA in the different plasma lipid classes differed substantially when ingested in the form of fish oil or liposomes. These results were interpreted in terms of different lipid bioavailability and metabolic fate during the digestive steps and in the liver, with the dietary source.     

Low-Field Nuclear Magnetic Resonance Time Domain Characterization of Polyunsaturated Fatty Acid–Rich Linseed and Fish Oil Emulsions during Thermal Air Oxidation

Linseed contains high levels of polyunsaturated fatty acids (PUFA), such as α-linolenic acid (> 50% ALA-18:3), that are naturally protected against thermal oxidation by their encapsulation within linseed oil bodies (OB) by multiple components including antioxidant proteins and mucilage emulsifying agents. Linseed OB emulsions (LSE) can be produced by grinding linseed seeds, adding water, adjusting pH, and sonication. This is a process that can encapsulate externally added PUFA to minimize their thermal oxidation, as it does for the intrinsic ALA PUFA. Fish oil (FO) encapsulation into this LSE platform to form linseed fish oil emulsions (LSFE) offers the possibility of a nutritive delivery system of the biologically essential FO PUFA eicosapentaenoic acid and docosahexaenoic acid. In this study, ¹H low-field nuclear magnetic resonance (LF-NMR) is used to characterize LSE's and LSFE's chemical and structural properties as well as their stability and changes under thermal oxidation (55 °C for 96 hours). ¹H LF-NMR data processing was developed to generate one-dimensional (1D) T₁ (spin–lattice), 1D T₂ (spin–spin), and 2D (T₁ vs. T₂) relaxation time spectra that can characterize OB emulsions and monitor their time domain fingerprints (spectrum peaks) of chemical and structural changes during the oxidation process. The ¹H LF-NMR analysis were further supported and correlated with conventional peroxide value test, self-diffusion, droplet size distribution, zeta potential estimation of surface stability, and gas chromatography–mass spectrometry analysis of fatty acid profile changes under thermal oxidation conditions. The 1D and 2D LF-NMR relaxation spectra showed that the LSE and LSFE did not suffer intense oxidation process, due to PUFA assembly in OB oxidative protection. These results were further confirmed by the supportive analytical methodologies. The results of this study demonstrate the efficacy of ¹H LF-NMR methodology to monitor PUFA's rich oil and emulsion thermal oxidation.     

无催化多不饱和脂肪酸甘油酯的合成和优化

针对传统工艺合成多不饱和脂肪酸甘油酯存在溶剂残留、后续处理复杂、环境污染严重的问题,提出无催化、无溶剂、减压的条件下直接用多不饱和脂肪酸（PUFA）与甘油脱水合成多不饱和脂肪酸甘油酯的绿色工艺．通过薄层色谱（TLC）、红外光谱（IR）和气相色谱一质谱联用仪（GC-MS）等手段表征了产物的组成．以多不饱和脂肪酸转化率为指标,探讨反应温度、反应时间、醇酸比（摩尔比）对多不饱和脂肪酸转化率的影响．实验数据采用Fortran程序进行分析,拟合回归方程,对实验条件进行优化．结果表明：无催化、无溶剂、减压工艺合成的多不饱和脂肪酸甘油酯主要是由多不饱和脂肪酸为碳链的甘一酯、甘二酯和甘三酯组成．通过二次回归正交试验研究得出,多不饱和脂肪酸甘油酯合成的最优工艺条件为：温度为194．28℃,时间5h,醇酸比0．94,其转化率为93．06％．回归方程得出的回归值与实验值的平均相对误差为3．62％,证实了利用二次回归正交实验设计求得的数学模型的可靠性．     

Sesamin modulation of lipid class and fatty acid profile in early juvenile teleost, Lates calcarifer, fed different dietary oils

Sesamin, a major sesame seed lignan, has diverse biological functions including the modulation of molecular actions in lipid metabolic pathways and reducing cholesterol levels. Vertebrates have different capacities to biosynthesize long-chain PUFA from dietary precursors and sesamin can enhance the biosynthesis of ALA to EPA and DHA in marine teleost. Early juvenile barramundi, Lates calcarifer, were fed for two weeks on diets rich in ALA or SDA derived from linseed or Echium plantagineum, respectively. Both diets contained phytosterols and less cholesterol compared with a standard fish oil-based diet. The growth rates were reduced in the animals receiving sesamin regardless of the dietary oil. However, the relative levels of n-3 LC-PUFA in total lipid, but not the phospholipid, increased in the whole body by up to 25% in animals fed on sesamin with ALA or SDA. Sesamin reduced the relative levels of triacylglycerols and increased polar lipid, and did not affect the relative composition of phospholipid subclasses or sterols. Sesamin is a potent modulator for LC-PUFA biosynthesis in animals, but probably will have more effective impact at advanced ages. By modulating certain lipid metabolic pathways, sesamin has probably disrupted the body growth and development of organs and tissues in early juvenile barramundi.     

Sources and Bioactive Properties of Conjugated Dietary Fatty Acids

The group of conjugated fatty acids known as conjugated linoleic acid (CLA) isomers have been extensively studied with regard to their bioactive potential in treating some of the most prominent human health malignancies. However, CLA isomers are not the only group of potentially bioactive conjugated fatty acids currently undergoing study. In this regard, isomers of conjugated α‐linolenic acid, conjugated nonadecadienoic acid and conjugated eicosapentaenoic acid, to name but a few, have undergone experimental assessment. These studies have indicated many of these conjugated fatty acid isomers commonly possess anti‐carcinogenic, anti‐adipogenic, anti‐inflammatory and immune modulating properties, a number of which will be discussed in this review. The mechanisms through which these bioactivities are mediated have not yet been fully elucidated. However, existing evidence indicates that these fatty acids may play a role in modulating the expression of several oncogenes, cell cycle regulators, and genes associated with energy metabolism. Despite such bioactive potential, interest in these conjugated fatty acids has remained low relative to the CLA isomers. This may be partly attributed to the relatively recent emergence of these fatty acids as bioactives, but also due to a lack of awareness regarding sources from which they can be produced. In this review, we will also highlight the common sources of these conjugated fatty acids, including plants, algae, microbes and chemosynthesis.     

Analysis of Fatty Acid and Lignan Composition of Indian Germplasm of Sesame to Evaluate Their Nutritional Merits

An attempt was made to individually analyze a germplasm collection of 54 indigenous Indian sesame cultivars for fatty acid and lignan composition of their seed oil by gas chromatography and high performance liquid chromatography, respectively. The entries varied in their fatty acid and lignan composition. The mean percentage contents of palmitic, stearic, oleic, linoleic and α‐linolenic acids ranged between 10–22, 5–10, 38–50, 18–43 and less than 1 whereas sesamol, sesamin and sesamolin scored between 3–37, 27–67, 20–59 of the total percentage of lignan, respectively. The highest percentage of α‐linolenic acid (ALA) was obtained in Var‐9 (1.3 % of the total fatty acids). Among the lignans, high sesamin content is considered to be significant, particularly in terms of long shelf life and nutraceutical value of sesame seed oil. The study has broadened our understanding related to differential biochemical composition of the rich sesame germplasms, thereby providing us with a useful groundwork for identifying potential targets and suitable cultivars for genetic engineering approaches to be undertaken in order to improve the nutritional quality of sesame oil, which in turn would be beneficial towards human health.