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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 December 2013) | Viewed by 94304

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Prof. Dr. Andrew Sinclair

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School of Medicine, Deakin University, Waum Ponds, VIC 3217, Australia
Interests: nutrition; functional foods; human health; neuroscience; omega 3 fatty acids
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Dear Colleagues,

Fatty acids play important roles in vertebrates, invertebrates, microbes and plants. In mammals they are found in cellular membranes as components of the phospholipids, as sources of energy (via beta-oxidation), as signaling molecules (certain polyunsaturated fatty acids such as arachidonic acid), as precursors to bioactive compounds in various tissues (eicosanoids, resolvins, neuroprotectins and related compounds), and as organic compounds capable of influencing gene expression in various tissues.
There continues to be controversy over which types of saturated fatty acids are ‘most harmful’; whether trans fatty acids from industrial sources or ruminant sources have the same biological properties; whether positional distribution of fatty acids on glycerol backbone of triacylglycerols is biologically meaningful; whether linoleic acid is as cardioprotective as previously thought; which omega 3 fatty acids are important to human health and whether medium chain fatty acids have a role in health? Furthermore, there is an ongoing debate about the capacity of humans and other species to effectively metabolise linolenic acid to the longer chain omega 3 fatty acid (DHA). In terms of brain health controversy exists over the roles of EPA and DHA (and even DPA) in development, depression and other neuropsychological disorders. It is still not clear how the polyunsaturated fatty acids are transported to the brain and how these are delivered to neurons, astrocytes and oligodendroglial cells.
Plants are capable of synthesizing a wide range of fatty acids, with much of these being stored in the seeds in the TAG form. Recent advances in gene technology has lead to the ‘engineering’ of the composition of the fatty acids in different oilseed plants. Furthermore, in plants, highly unsaturated fatty acids are precursors to hydroxy fatty acids, known as oxylipins, which play a role in inflammatory processes.
Fatty acids are found in microbes and generally are different to those present in mammals and plants, with straight chain, branched chain and monounsaturates predominating. There is a significant effort being made to identify species of microbes living in the marine environment as potential sources of long chain omega 3 fatty acids. Gut microbiota can make short chain fatty acids which are regarded as important for gut health, but is this the only property of these fatty acids in the gut (do they play a role systemically?).
A novel source of fatty acids has been created by the search for oil-bearing marine microalgae or phytoplankton, for omega 3 fatty acids or even as a potential biofuel. Certain fungi are also being used to produce polyunsaturated fatty acids such as arachidonic acid.
Recent developments in the application of lipidomic technologies have increased our understanding of the importance of these tools to allow much greater insight into the role of individual fatty acids in cells.
The objective of this special issue of Molecules is to highlight the latest breakthroughs in the exploration and in the applications of fatty acids, covering all aspects in different species of vertebrates, invertebrates, plants and micro-organisms.

Dr. Andrew Sinclair  
Guest Editor

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Keywords

saturated fatty acids
short chain fatty acids
medium chain fatty acids
monounsaturated fatty acids
trans fatty acids
hydroxy fatty acids
furan fatty acids
polyunsaturated fatty acids
omega 3 fatty acids
omega 6 fatty acids
biofuels
nutritional biochemistry
effects on gene, protein and metabolite expression
analytical chemistry, lipidomics
medical physiology

Published Papers (12 papers)

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Research

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1144 KiB

Open AccessArticle

Targeted Lipid Analysis of Haemolytic Mycelial Extracts of Aspergillus niger

by Maruša Novak, Kristina Sepčić, Nada Kraševec, Igor Križaj, Peter Maček, Gregor Anderluh, Graziano Guella and Ines Mancini

Molecules 2014, 19(7), 9051-9069; https://doi.org/10.3390/molecules19079051 - 30 Jun 2014

Cited by 7 | Viewed by 6787

Abstract

Ethanolic extracts of mycelia from Aspergillus niger (strain N402) grown in liquid media were observed to have haemolytic activity on bovine erythrocytes. This haemolytic activity decreased significantly during the time of growth (1–3 days). Moreover, when A. niger was grown on carbon-deprived medium, the efficiency of this haemolytic activity in the ethanolic extracts was much lower than when grown in carbon-enriched medium, and became almost undetectable after 3 days of growth in carbon-deprived medium. The lipid composition of these ethanolic extracts was analysed by liquid chromatography–electrospray ionisation tandem mass spectrometry. This haemolytic activity can be mainly linked to the relative levels of the molar ratios of the unsaturated fatty acids and lysophosphatidylcholines. Full article

(This article belongs to the Special Issue Fatty Acids)

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568 KiB

Open AccessArticle

Fatty Acids as a Tool to Understand Microbial Diversity and Their Role in Food Webs of Mediterranean Temporary Ponds

by Carla C. C. R. De Carvalho and Maria-José Caramujo

Molecules 2014, 19(5), 5570-5598; https://doi.org/10.3390/molecules19055570 - 30 Apr 2014

Cited by 34 | Viewed by 7756

Abstract

Temporary Mediterranean ponds are complex ecosystems which support a high diversity of organisms that include heterotrophic microorganisms, algae, crustaceans, amphibians and higher plants, and have the potential to supply food and a resting place to migratory birds. The role of heterotrophs at the base of the food web in providing energy to the higher trophic levels was studied in temporary ponds in Central and Southern Portugal. The relative quantification of the hetero and autotrophic biomass at the base of the food web in each pond was derived from the polar fatty acid (PLFA) composition of seston through the application of the matrix factorization program CHEMTAX that used specific PLFA and their relative proportion as markers for e.g., classes of bacteria, algae and fungi. The species composition of the culturable microbial communities was identified through their fatty acid profiles. The biomass in the lower trophic level of some ponds presented an even proportion of auto to heterotrophic organisms whilst either bacteria or algae dominated in others. In a selected subset of ponds, the incorporation of bacterial fatty acids was observed to occur in potentially herbivorous zooplankton crustacean. Zooplankton consumed and incorporated bacterial fatty acids into their body tissues, including into their phospholipids, which indicates that energy of heterotrophic origin contributes to the aquatic food webs of temporary ponds. Full article

(This article belongs to the Special Issue Fatty Acids)

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212 KiB

Open AccessArticle

Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

by Anne Marie Langseter, Yngve Stenstrøm and Lars Skattebøl

Molecules 2014, 19(3), 3804-3812; https://doi.org/10.3390/molecules19033804 - 24 Mar 2014

Cited by 8 | Viewed by 6441

Abstract

The synthesis of the marine natural product 1,6Z,9Z,12Z,15Z-octadecapentaen-3-one (1) has been achieved by two different routes starting from the ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively. Using EPA ethyl [...] Read more.

(This article belongs to the Special Issue Fatty Acids)

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Open AccessArticle

Omega-3 Fatty Acids Protect Renal Functions by Increasing Docosahexaenoic Acid-Derived Metabolite Levels in SHR.Cg-Lepr^cp/NDmcr Rats, a Metabolic Syndrome Model

by Masanori Katakura, Michio Hashimoto, Takayuki Inoue, Abdullah Al Mamun, Yoko Tanabe, Ryo Iwamoto, Makoto Arita, Satoru Tsuchikura and Osamu Shido

Molecules 2014, 19(3), 3247-3263; https://doi.org/10.3390/molecules19033247 - 17 Mar 2014

Cited by 28 | Viewed by 9462

Abstract

The omega-3 polyunsaturated fatty acids (ω-3 PUFAs) docosahexaenoic acid (DHA) and/or eicosapentaenoic acid (EPA) protect against diabetic nephropathy by inhibiting inflammation. The aim of this study was to assess the effects of highly purified DHA and EPA or EPA only administration on renal function and renal eicosanoid and docosanoid levels in an animal model of metabolic syndrome, SHR.Cg-Lepr^cp/NDmcr (SHRcp) rats. Male SHRcp rats were divided into 3 groups. Control (5% arabic gum), TAK-085 (300 mg/kg/day, containing 467 mg/g EPA and 365 mg/g DHA), or EPA (300 mg/kg/day) was orally administered for 20 weeks. The urinary albumin to creatinine ratio in the TAK-085-administered group was significantly lower than that in other groups. The glomerular sclerosis score in the TAK-085-administered group was significantly lower than that in the other groups. Although DHA levels were increased in total kidney fatty acids, the levels of nonesterified DHA were not significantly different among the 3 groups, whereas the levels of protectin D1, resolvin D1, and resolvin D2 were significantly increased in the TAK-085-administered group. The results show that the use of combination therapy with DHA and EPA in SHRcp rats improved or prevented renal failure associate with metabolic syndrome with decreasing triglyceride levels and increasing ω-3 PUFA lipid mediators. Full article

(This article belongs to the Special Issue Fatty Acids)

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284 KiB

Open AccessArticle

Fatty Acids from Pool Lipids as Possible Precursors of the Male Marking Pheromone in Bumblebees

by Edita Kofroňová, Adam Nekola, Josef Cvačka, Jiří Kindl and Irena Valterová

Molecules 2014, 19(2), 2330-2343; https://doi.org/10.3390/molecules19022330 - 21 Feb 2014

Cited by 4 | Viewed by 6571

Abstract

Triacylglycerols (TGs) stored in the fat bodies of bumblebee males have a species-specific composition. The striking structural similarities between TG fatty acids (FAs) and components of the male marking pheromone in certain species led to the hypothesis that FAs may serve as precursors in pheromone biosynthesis. Here, we analysed TGs from B. ruderatus, B. bohemicus, and B. campestris. Nonadec-9-ene and icos-15-en-1-ol are the main components of B. ruderatus labial gland secretion, forming up to 92% of the gland extract. The corresponding icos-11-enic and icos-15-enic acids were found in TGs at levels higher than usual for bumblebee species. We found similar relationships in B. campestris and B. bohemicus. These results suggest that FAs might be precursors of aliphatic compounds in the male pheromones. Furthermore, we report for the first time the pheromone structure of B. ruderatus males. Full article

(This article belongs to the Special Issue Fatty Acids)

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221 KiB

Open AccessArticle

Fatty Acid Profile of Cheese from Dairy Goats Fed a Diet Enriched with Castor, Sesame and Faveleira Vegetable Oils

by Ertha Medeiros, Rita Queiroga, Maria Oliveira, Ariosvaldo Medeiros, Mayara Sabedot, Marco Bomfim and Marta Madruga

Molecules 2014, 19(1), 992-1003; https://doi.org/10.3390/molecules19010992 - 15 Jan 2014

Cited by 53 | Viewed by 7860

Abstract

The addition of vegetable oils to the diets of dairy goats is an alternative to supplemental feeding during the dry period and improves the lipid profile of milk and by-products. Cheeses were produced using milk from cross bred goats (Saanen × Alpina) fed diets enriched with 4% vegetable oil (faveleira, sesame or castor), the fatty acid profile of cheeses was studied. Supplementation with vegetable oils did not increase the total fat percentage of the cheese (p ≥ 0.05) but did increase the percentage of CLA isomers, long-chain fatty acids (LCFA) and polyunsaturated fatty acids (PUFA); in addition, the index of desirable fatty acids (DFA - expressed as the sum of unsaturated fatty acids plus stearic acid) was increased for cheese made from milk from goats fed sesame or faveleira oil. Cheeses may have had increased percentages of cis-9,trans-11-CLA due to the supplementation of animal diets with vegetable oils rich in C18:2, such as faveleira and sesame oils. The fatty acid profile of goat cheese did not change significantly in response to the use of castor oil. Thus, the addition of sesame and faveleira oils to goat diets positively altered the fatty acid profile, which improved the nutritional characteristics of the fat present in goat cheese. Full article

(This article belongs to the Special Issue Fatty Acids)

1914 KiB

Open AccessArticle

Discrimination of Multi-Origin Chinese Herbal Medicines Using Gas Chromatography-Mass Spectrometry-Based Fatty Acid Profiling

by Xiao-Jing Zhang, Jian-Feng Qiu, Lan-Ping Guo, Ying Wang, Peng Li, Feng-Qing Yang, Huanxing Su and Jian-Bo Wan

Molecules 2013, 18(12), 15329-15343; https://doi.org/10.3390/molecules181215329 - 11 Dec 2013

Cited by 24 | Viewed by 6756

Abstract

Multi-origin Chinese herbal medicines, with herbs originating from more than one species of plants, is a common phenomenon but an important issue in Traditional Chinese Medicines (TCMs). In the present study, a gas chromatography-mass spectrometry (GC-MS)—based fatty acid profiling approach to rapidly discriminate multi-origin Chinese medicines in terms of species and medicinal parts was proposed and validated using tuberous roots (Curcumae Radix) and rhizomes (Curcumae Rhizoma and Curcumae Longae Rhizoma) derived from four Curcuma species (e.g., C. wenyujin, C. kwangsiensis, C. phaeocaulis and C. longa) as models. Both type and content of fatty acids varied among different species of either tuberous roots or rhizomes, indicating each species has its own fatty acid pattern. Orthogonal partial least squares discriminant analysis (OPLS-DA) and hierarchical clustering analysis (HCA) based on dataset of global fatty acid profiling showed that either tuberous roots or rhizomes samples could be clearly classified into four clusters according to their species. Furthermore, those tested samples could also be discriminated in terms of their medicinal parts (e.g., tuberous root and rhizome). Our findings suggest that the proposed GC-MS-based fatty acid profiling followed by multivariate statistical analysis provides a reliable platform to discriminate multi-origin Chinese herbal medicines according to species and medicinal parts, which will be helpful for ensuring their quality, safety and efficacy. Full article

(This article belongs to the Special Issue Fatty Acids)

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320 KiB

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Maternal High Fat Feeding Does Not Have Long-Lasting Effects on Body Composition and Bone Health in Female and Male Wistar Rat Offspring at Young Adulthood

by Paula M. Miotto, Laura M. Castelli, Foyinsola Amoye, Paul J. LeBlanc, Sandra J. Peters, Brian D. Roy and Wendy E. Ward

Molecules 2013, 18(12), 15094-15109; https://doi.org/10.3390/molecules181215094 - 06 Dec 2013

Cited by 17 | Viewed by 5742

Abstract

High fat diets adversely affect body composition, bone mineral and strength, and alter bone fatty acid composition. It is unclear if maternal high fat (HF) feeding permanently alters offspring body composition and bone health. Female rats were fed control (CON) or HF diet for 10 weeks, bred, and continued their diets throughout pregnancy and lactation. Male and female offspring were studied at weaning and 3 months, following consumption of CON diet. At weaning, but not 3 months of age, male and female offspring from dams fed HF diet had lower lean mass and higher fat and bone mass, and higher femur bone mineral density (females only) than offspring of dams fed CON diet. Male and female offspring femurs from dams fed HF diet had higher monounsaturates and lower n6 polyunsaturates at weaning than offspring from dams fed CON diet, where females from dams fed HF diet had higher saturates and lower n6 polyunsaturates at 3 months of age. There were no differences in strength of femurs or lumbar vertebrae at 3 months of age in either male or female offspring. In conclusion, maternal HF feeding did not permanently affect body composition and bone health at young adulthood in offspring. Full article

(This article belongs to the Special Issue Fatty Acids)

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296 KiB

Open AccessArticle

Multiplexed Analysis of Cage and Cage Free Chicken Egg Fatty Acids Using Stable Isotope Labeling and Mass Spectrometry

by Richard G. Torde, Andrew J. Therrien, Michael R. Shortreed, Lloyd M. Smith and Shane M. Lamos

Molecules 2013, 18(12), 14977-14988; https://doi.org/10.3390/molecules181214977 - 05 Dec 2013

Cited by 16 | Viewed by 7373

Abstract

Binary stable isotope labeling couple with LC-ESI-MS has been used as a powerful non-targeted approach for the relative quantification of lipids, amino acids, and many other important metabolite classes. A multiplexed approach using three or more isotopic labeling reagents greatly reduces analytical run-time while maintaining excellent sensitivity and reproducibility. Three isotopic cholamine labeling reagents have been developed to take advantage of the pre-ionized character of cholamine, for ESI, and the ease by which stable isotopes can be incorporated into the cholamine structure. These three cholamine labeling reagents have been used to relatively quantify three fatty acid samples simultaneously. The quantification resulted in the observation of 12 fatty acids that had an average absolute error of 0.9% and an average coefficient of variation of 6.1%. Caged versus cage-free isotope labeling experiments showed that cage-free eggs have an increased level of omega-3 fatty acids as compared to caged eggs. This multiplexed fatty acid analysis provides an inexpensive and expedited tool for broad-based lipid profiling that will further aid discoveries in the mechanisms of fatty acid action in cells. Full article

(This article belongs to the Special Issue Fatty Acids)

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Review

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830 KiB

Open AccessReview

20 Years of Fatty Acid Analysis by Capillary Electrophoresis

by Marcone Augusto Leal De Oliveira, Brenda Lee Simas Porto, Isaura Daniele Leite Faria, Patricia Lopes De Oliveira, Patricia Mendonça De Castro Barra, Renata De Jesus Coelho Castro and Renata Takabayashi Sato

Molecules 2014, 19(9), 14094-14113; https://doi.org/10.3390/molecules190914094 - 09 Sep 2014

Cited by 42 | Viewed by 8734

Abstract

A review taking into account the literature reports covering 20 years of fatty acid analysis by capillary electrophoresis is presented. This paper describes the evolution of fatty acid analysis using different CE modes such as capillary zone electrophoresis, non-aqueous capillary electrophoresis, micellar electrokinetic capillary chromatography and microemulsion electrokinetic chromatography employing different detection systems, such as ultraviolet-visible, capacitively coupled contactless conductivity, laser-induced fluorescence and mass spectrometry. In summary, the present review signals that CE seems to be an interesting analytical separation technique that is very useful for screening analysis or quantification of the usual fatty acids present in different matrices, offering short analysis times and a simple sample preparation step as inherent advantages in comparison with the classical methodology, making it a separation technique that is very attractive for quality control in industry and government agencies. Full article

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1421 KiB

Open AccessReview

Sensory TRP Channel Interactions with Endogenous Lipids and Their Biological Outcomes

by Sungjae Yoo, Ji Yeon Lim and Sun Wook Hwang

Molecules 2014, 19(4), 4708-4744; https://doi.org/10.3390/molecules19044708 - 15 Apr 2014

Cited by 19 | Viewed by 12266

Abstract

Lipids have long been studied as constituents of the cellular architecture and energy stores in the body. Evidence is now rapidly growing that particular lipid species are also important for molecular and cellular signaling. Here we review the current information on interactions between lipids and transient receptor potential (TRP) ion channels in nociceptive sensory afferents that mediate pain signaling. Sensory neuronal TRP channels play a crucial role in the detection of a variety of external and internal changes, particularly with damaging or pain-eliciting potentials that include noxiously high or low temperatures, stretching, and harmful substances. In addition, recent findings suggest that TRPs also contribute to altering synaptic plasticity that deteriorates chronic pain states. In both of these processes, specific lipids are often generated and have been found to strongly modulate TRP activities, resulting primarily in pain exacerbation. This review summarizes three standpoints viewing those lipid functions for TRP modulations as second messengers, intercellular transmitters, or bilayer building blocks. Based on these hypotheses, we discuss perspectives that account for how the TRP-lipid interaction contributes to the peripheral pain mechanism. Still a number of blurred aspects remain to be examined, which will be answered by future efforts and may help to better control pain states. Full article

(This article belongs to the Special Issue Fatty Acids)

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446 KiB

Open AccessReview

Investigating the Role of Polyunsaturated Fatty Acids in Bone Development Using Animal Models

by Beatrice Y.Y. Lau, Daniel J.A. Cohen, Wendy E. Ward and David W.L. Ma

Molecules 2013, 18(11), 14203-14227; https://doi.org/10.3390/molecules181114203 - 15 Nov 2013

Cited by 48 | Viewed by 7491

Abstract

Incorporating n-3 polyunsaturated fatty acids (PUFA) in the diet may promote the development of a healthy skeleton and thereby reduce the risk of developing osteoporosis in later life. Studies using developing animal models suggest lowering dietary n-6 PUFA and increasing n-3 PUFA intakes, especially long chain n-3 PUFA, may be beneficial for achieving higher bone mineral content, density and stronger bones. To date, the evidence regarding the effects of α-linolenic acid (ALA) remain equivocal, in contrast to evidence from the longer chain products, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). This review reports the results of investigations into n-3 PUFA supplementation on bone fatty acid composition, strength and mineral content in developing animal models as well as the mechanistic relationships of PUFA and bone, and identifies critical areas for future research. Overall, this review supports a probable role for essential (ALA) and long chain (EPA and DHA) n-3 PUFA for bone health. Understanding the role of PUFA in optimizing bone health may lead to dietary strategies that promote bone development and maintenance of a healthy skeleton. Full article

(This article belongs to the Special Issue Fatty Acids)

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