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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Food Chemistry".

Deadline for manuscript submissions: closed (15 November 2022) | Viewed by 28720

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Dr. Gangcheng Wu

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Guest Editor

School of Food Science and Technology, Jiangnan University, Wuxi, China
Interests: oil and fat; oil seeds; minor components in vegetable oil; frying; structured lipids; structured lipids; synthesis; health benefits
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Oils and fats, being an important source of fat-soluble nutrients, essential fatty acids, as well as energy, are daily consumed by humans. Lipids from natural sources are mainly composed of triacylglycerol (95%~98%) and minor components, such as tocochromanols, phytosterols, phenolic compounds, and squalene, and the previous studies have observed that most of these minor components have antioxidant properties. Moreover, the current research is mainly focusing on the physiological and biological activities of lipids and their possible relationships with human health. In addition, in the food industry, oils and fats could also provide numerous lipid-based foods, such as bread, biscuit, chocolate, margarine, and frozen dessert, with the desirable texture, flavor, and taste. However, the properties, quality and oxidative stability of food products are significantly influenced by fatty acid and triacylglycerol composition, due to the different physico-chemical properties, including melting behavior, crystallization, solid fat content, and interfacial and rheological properties.

This Special Issue will include original research articles, reviews, and short communications related to the health benefits, physicochemical properties, synthesis, processing, oxidation, nutrition and biotechnology of lipids, but are not limited to the above.

Dr. Gangcheng Wu
Guest Editor

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Keywords

lipids
minor components
processing
health benefits
nutrition
synthesis
oxidation

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Published Papers (10 papers)

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Research

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14 pages, 1029 KiB

Open AccessArticle

Impact of Gamma Irradiation and Kale Leaf Powder on Amino Acid and Fatty Acid Profiles of Chicken Meat under Different Storage Intervals

by Waseem Khalid, Muhammad Sajid Arshad, Gulzar Ahmad Nayik, Saleh Alfarraj, Mohammad Javed Ansari and Raquel P. F. Guiné

Molecules 2022, 27(23), 8201; https://doi.org/10.3390/molecules27238201 - 24 Nov 2022

Cited by 5 | Viewed by 2000

Abstract

The present study was planned to determine the effect of kale leaf powder and gamma rays on variations in the pH, amino acid and fatty acid profiles of chicken meat at different storage intervals. Significant changes (p ≤ 0.05) in the pH, amino acid and fatty acid profiles of chicken meat following different treatments (KLP (1% and 2%) and gamma irradiation (3k Gy)) were reported at 0, 7 and 14 days of storage. The pH value of the chicken meat sample decreased with the addition of kale leaf powder, whereas the value increased following a gamma irradiation dose of 3 kGy and with the passage of time. During different storage intervals, the minimum reduction in the amino acid and fatty acid quantities in the chicken meat samples was reported after gamma irradiation treatment. However, with the addition of KLP, the amount of amino acids and fatty acids in the chicken meat samples increased. Conclusively, the pH was observed to be reduced in the meat following combined treatment (irradiation + KLP), whereas the 2% KLP treatment improved the amino acid and fatty acid profiles of the chicken samples. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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13 pages, 1557 KiB

Open AccessArticle

Fatty Acids of Ten Commonly Consumed Pulses

by William Craig Byrdwell and Robert J. Goldschmidt

Molecules 2022, 27(21), 7260; https://doi.org/10.3390/molecules27217260 - 26 Oct 2022

Cited by 3 | Viewed by 2261

Abstract

Gas chromatography (GC) with flame ionization detection (FID) and mass spectrometry (MS) detection were used to characterize the fatty acid (FA) compositions of ten commonly consumed (i.e., market class) pulses. Lipids from ground pulses were extracted using a classical chloroform/methanol extraction and quantified by GC-FID with structural confirmation by GC-MS. Principal component analysis (PCA) was applied to FA compositions of the pulse extracts, and the pulses clustered into three distinct groups: one rich in linolenic acid, 18:3 (carbon number:unsaturation, C:U), one rich in 16:0, and one in which 18:1 was highest, along with predominant 18:2. These ten pulses averaged 46.1% linoleic acid (18:2), 22.7% oleic acid (18:1), 18.0% palmitic acid (16:0), and 7.6% linolenic acid (18:3). Individual values ranged widely, with 18:2 ranging from 26.0% in black beans to 48.4% in garbanzo beans. The greatest difference was in 18:3, which ranged from 2.2% in garbanzo beans to 38.8% in pinto beans. Oxo-FA were observed in all ten samples, and the distribution of oxo-FA in the samples also varied. Overall, the very different FA compositions of pulses lead to the possibility of breeding and genetic modification between pulses to produce the most desirable FA composition for nutritional benefit. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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16 pages, 2950 KiB

Open AccessFeature PaperArticle

Monitoring the Shelf Life of Refined Vegetable Oils under Market Storage Conditions—A Kinetic Chemofoodmetric Approach

by Sandra Martín-Torres, Juan Antonio Tello-Jiménez, Rafael López-Blanco, Antonio González-Casado and Luis Cuadros-Rodríguez

Molecules 2022, 27(19), 6508; https://doi.org/10.3390/molecules27196508 - 2 Oct 2022

Cited by 1 | Viewed by 2341

Abstract

Most physicochemical and sensory properties of edible vegetable oils are not stable over time. One of the main causes of quality depletion of vegetable oils is oxidation, which influences sensory acceptability and nutritional value, and could even lead to toxic compounds. That negative influence affects international refined oil prices and the variety of its culinary applications. Modelling quality depletion of vegetable oils and establishing the shelf life, generally accepted as the time until rancidity becomes evident, already remains a challenge for the industry. Hence, this paper will show a promising chemofoodmetric methodology, as an easy and straightforward tool to estimate the current shelf-life of refined vegetable oils, based on a comprehensive characterisation of quality depletion-related changes over storage time under real market conditions. The methodology for building a multivariate kinetic ageing-based model is described, taking into account all time-related physicochemical parameters and chemometric processing tools. From a particular ageing state, multiparametric models are able to reliably infer the expected storage time for each vegetable oil so that it remains consistent with acceptability requirements. The results of the study pointed out the accuracy of multivariate shelf-life modelling with regard to univariate modelling. Discrepancies were found in the oxidation rates of oils extracted from different plant seeds. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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12 pages, 2775 KiB

Open AccessArticle

Associations of Region and Lactation Stage with Odd-Chain Fatty Acid Profile in Triglycerides of Breast Milk in China

by Yiren Zhang, Hui Zhang, Emad Karrar, Wei Wei, Wei Zeng, Qingzhe Jin and Xingguo Wang

Molecules 2022, 27(19), 6324; https://doi.org/10.3390/molecules27196324 - 26 Sep 2022

Cited by 1 | Viewed by 1731

Abstract

Odd-chain fatty acids (OCFAs), with potential value for growing infants, have been reported in breast milk. The association of location and lactation stage with the profile and content of OCFAs in breast milk was studied. We analyzed 1487 breast milk samples collected from 12 areas in China, and 102 infant formulas from different brands were purchased from the local supermarket. The content of sn-2 C15:0 significantly decreased from the colostrum to the mature stage, while that of C17:0 was not significantly increased by the lactation stage (p > 0.05). The content of C15:0 and C17:0 significantly decreased dramatically after the colostrum period, while the content of C13:0 was highest in the mature stage. The level of C15:0 and C17:0 in human milk from Gansu and Xinjiang was significantly higher than that from other areas. Similar trends were observed on the level of sn-2 C15:0 and C17:0, whereas the content of sn-2 C11:0 and C13:0 was significantly higher in breast milk from Shandong. Based on the PDS-LA analysis, the difference among infant formulas, each stage of human milk and human milk from different locations were different. Research is needed to determine if there are health benefits associated with OCFAs. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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10 pages, 721 KiB

Open AccessCommunication

Cold-Pressed Pomegranate Seed Oil: Study of Punicic Acid Properties by Coupling of GC/FID and FTIR

by Aleksandra Zielińska, Krzysztof Wójcicki, Dorota Klensporf-Pawlik, Marta Marzec, Massimo Lucarini, Alessandra Durazzo, Joel Fonseca, Antonello Santini, Izabela Nowak and Eliana B. Souto

Molecules 2022, 27(18), 5863; https://doi.org/10.3390/molecules27185863 - 9 Sep 2022

Cited by 12 | Viewed by 3339

Abstract

Over the last decades, we have witnessed an increasing interest in food-related products containing vegetable oils. These oils can be obtained either by extraction or by mechanical pressing of different parts of plants (e.g., seeds, fruit, and drupels). Producers of nutraceuticals have ceaselessly searched for unique and effective natural ingredients. The enormous success of argan oil has been followed by discoveries of other interesting vegetable oils (e.g., pomegranate oil) containing several bioactives. This work describes the pomegranate fruit extract and seed oil as a rich source of conjugated linolenic acid as a metabolite of punicic acid (PA), deriving from the omega-5 family (ω-5). Through the chemical characterization of PA, its nutritional and therapeutic properties are highlighted together with the physiological properties that encourage its use in human nutrition. We analyzed the composition of all fatty acids with beneficial properties occurring in pomegranate seed oil using gas chromatography (GC) with flame-ionization detection (FID) analysis combined with Fourier transform infrared spectroscopy (FTIR). Pomegranate seed oil mainly consists of 9,11,13-octadic-trienoic acid (18:3), corresponding to 73 wt % of the total fatty acids. Nine components were identified by GC in PSO, varying between 0.58 and 73.19 wt %. Using midinfrared (MIR) spectroscopy, we compared the composition of pomegranate seed oil with that of meadowfoam seed oil (MSO), which is also becoming increasingly popular in the food industry due to its high content of long chain fatty acids (C20-22), providing increased oil stability. From the results of FTIR and MIR spectroscopy, we found that punicic acid is unique in PSO (73.19 wt %) but not in MSO. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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13 pages, 2508 KiB

Open AccessArticle

Exploring The Relative Astringency of Tea Catechins and Distinct Astringent Sensation of Catechins and Flavonol Glycosides via an In Vitro Assay Composed of Artificial Oil Bodies

by Chao-Tzu Liu and Jason T.C. Tzen

Molecules 2022, 27(17), 5679; https://doi.org/10.3390/molecules27175679 - 2 Sep 2022

Cited by 7 | Viewed by 2387

Abstract

Artificial oil bodies covered by a recombinant surface protein, caleosin fused with histatin 3 (a major human salivary peptide), were employed to explore the relative astringency of eight tea catechins. The results showed that gallate-type catechins were more astringent than non-gallate-type catechins, with an astringency order of epicatechin gallate > epigallocatechin gallate > gallocatechin gallate > catechin gallate > epigallocatechin > epicatechin > gallocatechin > catechin. As expected, the extension of brewing time led to an increase in catechin content in the tea infusion, thus elevating tea astringency. Detailed analysis showed that the enhanced proportion of gallate-type catechins was significantly higher than that of non-gallate-type catechins, indicating that tea astringency was elevated exponentially, rather than proportionally, when brewing time was extended. Rough surfaces were observed on artificial oil bodies when they were complexed with epigallocatechin gallate (a catechin), while a smooth surface was observed on those complexed with rutin (a flavonol glycoside) under an atomic force microscope and a scanning electron microscope. The results indicate that catechins and flavonol glycosides induce the sensation of rough (puckering) and smooth (velvety) astringency in tea, respectively. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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14 pages, 3827 KiB

Open AccessArticle

Elucidation of Olive Oil Oxidation Mechanisms by Analysis of Triacylglycerol Hydroperoxide Isomers Using LC-MS/MS

by Hayato Takahashi, Shunji Kato, Naoki Shimizu, Yurika Otoki, Junya Ito, Masayoshi Sakaino, Takashi Sano, Jun Imagi and Kiyotaka Nakagawa

Molecules 2022, 27(16), 5282; https://doi.org/10.3390/molecules27165282 - 18 Aug 2022

Cited by 4 | Viewed by 2276

Abstract

Despite the importance of the insight about the oxidation mechanisms (i.e., radical and singlet oxygen (¹O₂) oxidation) in extra virgin olive oil (EVOO), the elucidation has been difficult due to its various triacylglycerol molecular species and complex matrix. This study tried to evaluate the mechanisms responsible for EVOO oxidation in our daily use by quantitative determination of triacylglycerol hydroperoxide (TGOOH) isomers using LC-MS/MS. The standards of dioleoyl-(hydroperoxy octadecadienoyl)-triacylglycerol and dioleoyl-(hydroperoxy octadecamonoenoyl)-triacylglycerol, which are the predominant TGOOHs contained in EVOO, were prepared. Subsequently, fresh, thermal-, and photo-oxidized EVOO were analyzed. The obtained results mostly agreed with the previously reported characteristics of the radical and ¹O₂ oxidation of linoleic acid and oleic acid. This suggests that the methods described in this paper should be valuable in understanding how different factors that determine the quality of EVOO (e.g., olive species, cultivation area, cultivation timing, and extraction methods) contribute to its oxidative stability. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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11 pages, 550 KiB

Open AccessArticle

Comparison of Different Extraction Processes on the Physicochemical Properties, Nutritional Components and Antioxidant Ability of Xanthoceras sorbifolia Bunge Kernel Oil

by Yuling Zheng, Pan Gao, Shu Wang, Yuling Ruan, Wu Zhong, Chuanrong Hu and Dongping He

Molecules 2022, 27(13), 4185; https://doi.org/10.3390/molecules27134185 - 29 Jun 2022

Cited by 7 | Viewed by 2412

Abstract

In this study, we investigated and compared the oil yield, physicochemical properties, fatty acid composition, nutrient content, and antioxidant ability of Xanthoceras sorbifolia Bunge (X. sorbifolia) kernel oils obtained by cold-pressing (CP), hexane extraction (HE), aqueous enzymatic extraction (AEE), and supercritical fluid extraction (SFE). The results indicated that X. sorbifolia oil contained a high percentage of monounsaturated fatty acids (49.31–50.38%), especially oleic acid (30.73–30.98%) and nervonic acid (2.73–3.09%) and that the extraction methods had little effect on the composition and content of fatty acids. X. sorbifolia oil is an excellent source of nervonic acid. Additionally, the HE method resulted in the highest oil yield (98.04%), oxidation stability index (9.20 h), tocopherol content (530.15 mg/kg) and sterol content (2104.07 mg/kg). The DPPH scavenging activity rates of the oil produced by SFE was the highest. Considering the health and nutritional value of oils, HE is a promising method for X. sorbifolia oil processing. According to multiple linear regression analysis, the antioxidant capacity of the oil was negatively correlated with sterol and stearic acid content and positively correlated with linoleic acid, arachidic acid and polyunsaturated fatty acid content. This information is important for improving the nutritional value and industrial production of X. sorbifolia. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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14 pages, 2226 KiB

Open AccessArticle

Physicochemical, Antioxidant and Anticancer Characteristics of Seed Oil from Three Chenopodium quinoa Genotypes

by Yingbin Shen, Liyou Zheng, Yao Peng, Xucheng Zhu, Fu Liu, Xinquan Yang and Haimei Li

Molecules 2022, 27(8), 2453; https://doi.org/10.3390/molecules27082453 - 11 Apr 2022

Cited by 23 | Viewed by 3175

Abstract

Chenopodium quinoa Willd. is recognized to be an excellent nutrient with high nutritional content. However, few genotypes of quinoa were analyzed, so we found a knowledge gap in the comparison of quinoa seeds of different genotypes. This study aims to compare the physicochemical, antioxidant, and anticancer properties of seed oil from three C. quinoa genotypes. Seeds of three genotypes (white, red, and black) were extracted with hexane and compared in this study. The oil yields of these quinoa seeds were 5.68–6.19% which contained predominantly polyunsaturated fatty acids (82.78–85.52%). The total tocopherol content ranged from 117.29 to 156.67 mg/kg and mainly consisted of γ-tocopherol. Total phytosterols in the three oils ranged from 9.4 to 12.2 g/kg. Black quinoa seed oil had the highest phytosterols followed by red and white quinoas. The chemical profile of quinoa seed oils paralleled by their antioxidant and anticancer activities in vitro was positively correlated with the seed coat color. Black quinoa seed oil had the best antioxidant and anti-proliferation effect on HCT 116 cells by the induction of apoptosis in a dose-dependent manner, which may play more significant roles in the chemoprevention of cancer and other diseases related to oxidative stress as a source of functional foods. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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Review

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31 pages, 2833 KiB

Open AccessReview

Highly Valuable Fish Oil: Formation Process, Enrichment, Subsequent Utilization, and Storage of Eicosapentaenoic Acid Ethyl Esters

by Mengyuan Yi, Yue You, Yiren Zhang, Gangcheng Wu, Emad Karrar, Le Zhang, Hui Zhang, Qingzhe Jin and Xingguo Wang

Molecules 2023, 28(2), 672; https://doi.org/10.3390/molecules28020672 - 9 Jan 2023

Cited by 12 | Viewed by 5270

Abstract

In recent years, as the demand for precision nutrition is continuously increasing, scientific studies have shown that high-purity eicosapentaenoic acid ethyl ester (EPA-EE) functions more efficiently than mixed omega-3 polyunsaturated fatty acid preparations in diseases such as hyperlipidemia, heart disease, major depression, and heart disease; therefore, the market demand for EPA-EE is growing by the day. In this paper, we attempt to review EPA-EE from a whole-manufacturing-chain perspective. First, the extraction, refining, and ethanolysis processes (fish oil and ethanol undergo transesterification) of EPA-EE are described, emphasizing the potential of green substitute technologies. Then, the method of EPA enrichment is thoroughly detailed, the pros and cons of different methods are compared, and current developments in monomer production techniques are addressed. Finally, a summary of current advanced strategies for dealing with the low oxidative stability and low bioavailability of EPA-EE is presented. In conclusion, understanding the entire production process of EPA-EE will enable us to govern each step from a macro perspective and accomplish the best use of EPA-EE in a more cost-effective and environmentally friendly way. Full article

(This article belongs to the Special Issue Lipids in Food Chemistry)

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