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Marine Lipids 2017

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A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (31 August 2017) | Viewed by 64476

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Dr. Maria do Rosário Domingues

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CESAM—Centre for Environmental and Marine Studies & Department of Chemistry, University of Aveiro, Aveiro, Portugal
Interests: mass spectrometry lipidomics; marine lipidomics; lipidomics in health and disease; food lipidomics; microbial lipidomics glycomics; biomolecules modification associated with oxidative stress monitored by mass spectrometry
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Dr. Ricardo Calado

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ECOMARE & CESAM & Department of Biology, University of Aveiro, 3810-193 Aveiro, Portugal
Interests: fatty acids; LC-PUFA; marine invertebrates; DHA; marine biotechnology; marine aquaculture
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Prof. Dr. Pedro Domingues

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Mass Spectrometry Centre, Chemistry Department &QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal
Interests: mass spectrometry; liquid chromatography-mass spectrometry; lipidomics; proteomics; oxidative stress
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Special Issue Information

Dear Colleagues,

Marine organisms are a well-known source of lipids with high nutritional value, such as n-3 fatty acids (e.g., 20:5 and 22:6), but also possess bioactive properties (e.g., polar lipids as glycolipids and phospholipids). Polar lipids are considered high added value bioactive molecules with health promoting effects, and with potential applications in food, feed, and pharmaceutical industries. Although some polar lipids of marine organisms are known to have functional properties (e.g., anti-inflammatory, anti-proliferative, antioxidant and antimicrobial), to potential of these molecules is yet to be fully unravelled, as the lipidome of the majority of marine organisms remains largely unknown. Different marine organisms, even when closely related in the tree of life, display specific lipidome signatures, which are representative of the remarkable chemical biodiversity present in world oceans. Lipid composition can also change due to environmental and nutritional conditions. If one considers that each marine organism contains thousands of structurally and functionally diverse lipids, it is clear that the characterization of their lipidome is a challenging task. Nonetheless, in recent years, advanced analytical approaches coupling chromatography and mass spectrometry emerged as powerful tools in lipidomic analysis. The resolution and high throughput analysis achieved with these analytical approaches has allowed researchers to identify and quantify the lipid species present on the cells and tissues of a diversity of marine organisms, opening new perspectives in the identification of lipid signatures for their valorisation and biotechnological applications.

This Special Issue, “Marine Lipids II, 2017”, will highlight innovative approaches and new findings on the lipidomics of marine organism, with emphasis on their valorization.

Dr. Rosário Domingues
Dr. Ricardo Calado
Dr. Pedro Domingues
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Marine Drugs is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

lipids
lipidomics
glycolipids
phospholipids
oxylipins
fatty acids
marine organisms
bioactivity

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Published Papers (10 papers)

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1162 KiB

Open AccessArticle

The Marine Fungi Rhodotorula sp. (Strain CNYC4007) as a Potential Feed Source for Fish Larvae Nutrition

by M. Barra, A. Llanos-Rivera, F. Cruzat, N. Pino-Maureira and R. R. González-Saldía

Mar. Drugs 2017, 15(12), 369; https://doi.org/10.3390/md15120369 - 1 Dec 2017

Cited by 2 | Viewed by 4657

Abstract

Fish oil is used in the production of feed for cultured fish owing to its high polyunsaturated fatty acid content (PUFA). The over-exploitation of fisheries and events like “El Niño” are reducing the fish oil supply. Some marine microorganisms are considered potentially as alternative fatty acid sources. This study assesses a strain of Rhodotorula sp. (strain CNYC4007; 27% docosahexaenoic acid (DHA) of total fatty acids), as feed for fish larvae. The total length and ribonucleic acid (RNA)/deoxyribonucleic acid (DNA) ratio of Danio rerio larvae was determined at first feeding at six and 12 days old (post-yolk absorption larvae). Larvae fed with microencapsulated Rhodotorula sp. CNYC4007 had a significantly higher RNA/DNA ratio than control group (C1). At six days post-yolk absorption group, the RNA/DNA ratio of larvae fed with Rhodotorula sp. bioencapsulated in Brachionus sp. was significantly higher than control group fed with a commercial diet high in DHA (C2-DHA). Finally, at 12 days post-yolk absorption, the RNA/DNA ratio was significantly higher in larvae fed with Rhodotorula sp. CNYC4007 and C2-DHA (both bioencapsulated in Artemia sp. nauplii) than in control group (C1). These results suggest that Rhodotorula sp. CNYC4007 can be an alternative source of DHA for feeding fish at larval stage, providing a sustainable source of fatty acids. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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Open AccessArticle

Chemical Profiling and Bioactivity of Body Wall Lipids from Strongylocentrotus droebachiensis

by Alexander N. Shikov, Into Laakso, Olga N. Pozharitskaya, Tuulikki Seppänen-Laakso, Anna S. Krishtopina, Marina N. Makarova, Heikki Vuorela and Valery Makarov

Mar. Drugs 2017, 15(12), 365; https://doi.org/10.3390/md15120365 - 24 Nov 2017

Cited by 10 | Viewed by 5961

Abstract

The lipids from gonads and polyhydroxynaphthoquinone pigments from body walls of sea urchins are intensively studied. However, little is known about the body wall (BW) lipids. Ethanol extract (55 °C) contained about equal amounts of saturated (SaFA) and monounsaturated fatty acids (MUFA) representing 60% of total fatty acids, with myristic, palmitic and eicosenoic acids as major SaFAs and MUFAs, respectively. Non-methylene-interrupted dienes (13%) were composed of eicosadienoic and docosadienoic acids. Long-chain polyunsaturated fatty acids (LC-PUFA) included two main components, n6 arachidonic and n3 eicosapentaenoic acids, even with equal concentrations (15 μg/mg) and a balanced n6/n3 PUFA ratio (0.86). The UPLC-ELSD analysis showed that a great majority of the lipids (80%) in the ethanolic extract were phosphatidylcholine (60 μg/mg) and phosphatidylethanolamine (40 μg/mg), while the proportion of neutral lipids remained lower than 20%. In addition, alkoxyglycerol derivatives—chimyl, selachyl, and batyl alcohols—were quantified. We have assumed that the mechanism of action of body wall lipids in the present study is via the inhibition of MAPK p38, COX-1, and COX-2. Our findings open the prospective to utilize this lipid fraction as a source for the development of drugs with anti-inflammatory activity. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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Open AccessFeature PaperArticle

Lipophilic Fraction of Cultivated Bifurcaria bifurcata R. Ross: Detailed Composition and In Vitro Prospection of Current Challenging Bioactive Properties

by Sónia A. O. Santos, Stephanie S. Trindade, Catia S. D. Oliveira, Paula Parreira, Daniela Rosa, Maria F. Duarte, Isabel Ferreira, Maria T. Cruz, Andreia M. Rego, Maria H. Abreu, Silvia M. Rocha and Armando J. D. Silvestre

Mar. Drugs 2017, 15(11), 340; https://doi.org/10.3390/md15110340 - 1 Nov 2017

Cited by 26 | Viewed by 6064

Abstract

Macroalgae have been seen as an alternative source of molecules with promising bioactivities to use in the prevention and treatment of current lifestyle diseases. In this vein, the lipophilic fraction of short-term (three weeks) cultivated Bifurcaria bifurcata was characterized in detail by gas chromatography–mass spectrometry (GC-MS). B. bifurcata dichloromethane extract was composed mainly by diterpenes (1892.78 ± 133.97 mg kg⁻¹ dry weight (DW)), followed by fatty acids, both saturated (550.35 ± 15.67 mg kg⁻¹ DW) and unsaturated (397.06 ± 18.44 mg kg⁻¹ DW). Considerable amounts of sterols, namely fucosterol (317.68 ± 26.11 mg kg⁻¹ DW) were also found. In vitro tests demonstrated that the B. bifurcata lipophilic extract show antioxidant, anti-inflammatory and antibacterial activities (against both Gram-positive and Gram-negative bacteria), using low extract concentrations (in the order of µg mL⁻¹). Enhancement of antibiotic activity of drug families of major clinical importance was observed by the use of B. bifurcata extract. This enhancement of antibiotic activity depends on the microbial strain and on the antibiotic. This work represents the first detailed phytochemical study of the lipophilic extract of B. bifurcata and is, therefore, an important contribution for the valorization of B. bifurcata macroalgae, with promising applications in functional foods, nutraceutical, cosmetic and biomedical fields. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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Open AccessArticle

Antibacterial Effect of Eicosapentaenoic Acid against Bacillus cereus and Staphylococcus aureus: Killing Kinetics, Selection for Resistance, and Potential Cellular Target

by Phuc Nguyen Thien Le and Andrew P. Desbois

Mar. Drugs 2017, 15(11), 334; https://doi.org/10.3390/md15110334 - 1 Nov 2017

Cited by 27 | Viewed by 5920

Abstract

Polyunsaturated fatty acids, such as eicosapentaenoic acid (EPA; C20:5n-3), are attracting interest as possible new topical antibacterial agents, particularly due to their potency and perceived safety. However, relatively little is known of the underlying mechanism of antibacterial action of EPA or whether bacteria can develop resistance quickly against this or similar compounds. Therefore, the aim of this present study was to determine the mechanism of antibacterial action of EPA and investigate whether bacteria could develop reduced susceptibility to this fatty acid upon repeated exposure. Against two common Gram-positive human pathogens, Bacillus cereus and Staphylococcus aureus, EPA inhibited bacterial growth with a minimum inhibitory concentration of 64 mg/L, while minimum bactericidal concentrations were 64 mg/L and 128 mg/L for B. cereus and S. aureus, respectively. Both species were killed completely in EPA at 128 mg/L within 15 min at 37 °C, while reduced bacterial viability was associated with increased release of 260-nm-absorbing material from the bacterial cells. Taken together, these observations suggest that EPA likely kills B. cereus and S. aureus by disrupting the cell membrane, ultimately leading to cell lysis. Serial passage of the strains in the presence of sub-inhibitory concentrations of EPA did not lead to the emergence or selection of strains with reduced susceptibility to EPA during 13 passages. This present study provides data that may support the development of EPA and other fatty acids as antibacterial agents for cosmetic and pharmaceutical applications. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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Open AccessArticle

Variation Quality and Kinetic Parameter of Commercial n-3 PUFA-Rich Oil during Oxidation via Rancimat

by Kai-Min Yang and Po-Yuan Chiang

Mar. Drugs 2017, 15(4), 97; https://doi.org/10.3390/md15040097 - 28 Mar 2017

Cited by 20 | Viewed by 5514

Abstract

Different biological sources of n-3 polyunsaturated fatty acids (n-3 PUFA) in mainstream commercial products include algae and fish. Lipid oxidation in n-3 PUFA-rich oil is the most important cause of its deterioration. We investigated the kinetic parameters of n-3 PUFA-rich oil during oxidation via Rancimat (at a temperature range of 70~100 °C). This was done on the basis of the Arrhenius equation, which indicates that the activation energies (Ea) for oxidative stability are 82.84–96.98 KJ/mol. The chemical substrates of different oxidative levels resulting from oxidation via Rancimat at 80 °C were evaluated. At the initiation of oxidation, the tocopherols in the oil degraded very quickly, resulting in diminished protection against further oxidation. Then, the degradation of the fatty acids with n-3 PUFA-rich oil was evident because of decreased levels of PUFA along with increased levels of saturated fatty acids (SFA). The quality deterioration from n-3 PUFA-rich oil at the various oxidative levels was analyzed chemometrically. The anisidine value (p-AV, r: 0.92) and total oxidation value (TOTOX, r: 0.91) exhibited a good linear relationship in a principal component analysis (PCA), while oxidative change and a significant quality change to the induction period (IP) were detected through an agglomerative hierarchical cluster (AHC) analysis. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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3420 KiB

Open AccessArticle

An Extract from Shrimp Processing By-Products Protects SH-SY5Y Cells from Neurotoxicity Induced by Aβ_25–35

by Yongping Zhang, Guangling Jiao, Cai Song, Shelly Gu, Richard E. Brown, Junzeng Zhang, Pingcheng Zhang, Jacques Gagnon, Steven Locke, Roumiana Stefanova, Claude Pelletier, Yi Zhang and Hongyu Lu

Mar. Drugs 2017, 15(3), 83; https://doi.org/10.3390/md15030083 - 22 Mar 2017

Cited by 20 | Viewed by 6904

Abstract

Increased evidence suggests that marine unsaturated fatty acids (FAs) can protect neurons from amyloid-β (Aβ)-induced neurodegeneration. Nuclear magnetic resonance (NMR), high performance liquid chromatography (HPLC) and gas chromatography (GC) assays showed that the acetone extract 4-2A obtained from shrimp Pandalus borealis industry processing wastes contained 67.19% monounsaturated FAs and 16.84% polyunsaturated FAs. The present study evaluated the anti-oxidative and anti-inflammatory effects of 4-2A in Aβ_25–35-insulted differentiated SH-SY5Y cells. Cell viability and cytotoxicity were measured by using 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assays. Quantitative PCR and Western blotting were used to study the expression of neurotrophins, pro-inflammatory cytokines and apoptosis-related genes. Administration of 20 μM Aβ_25–35 significantly reduced SH-SY5Y cell viability, the expression of nerve growth factor (NGF) and its tyrosine kinase TrkA receptor, as well as the level of glutathione, while increased reactive oxygen species (ROS), nitric oxide, tumor necrosis factor (TNF)-α, brain derived neurotrophic factor (BDNF) and its TrkB receptor. Aβ_25–35 also increased the Bax/Bcl-2 ratio and Caspase-3 expression. Treatment with 4-2A significantly attenuated the Aβ_25–35-induced changes in cell viability, ROS, GSH, NGF, TrkA, TNF-α, the Bax/Bcl-2 ratio and Caspase-3, except for nitric oxide, BDNF and TrKB. In conclusion, 4-2A effectively protected SH-SY5Y cells against Aβ-induced neuronal apoptosis/death by suppressing inflammation and oxidative stress and up-regulating NGF and TrKA expression. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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Open AccessArticle

Biosynthesis of Polyunsaturated Fatty Acids in Octopus vulgaris: Molecular Cloning and Functional Characterisation of a Stearoyl-CoA Desaturase and an Elongation of Very Long-Chain Fatty Acid 4 Protein

by Óscar Monroig, Rosa De Llanos, Inmaculada Varó, Francisco Hontoria, Douglas R. Tocher, Sergi Puig and Juan C. Navarro

Mar. Drugs 2017, 15(3), 82; https://doi.org/10.3390/md15030082 - 21 Mar 2017

Cited by 41 | Viewed by 6641

Abstract

Polyunsaturated fatty acids (PUFAs) have been acknowledged as essential nutrients for cephalopods but the specific PUFAs that satisfy the physiological requirements are unknown. To expand our previous investigations on characterisation of desaturases and elongases involved in the biosynthesis of PUFAs and hence determine the dietary PUFA requirements in cephalopods, this study aimed to investigate the roles that a stearoyl-CoA desaturase (Scd) and an elongation of very long-chain fatty acid 4 (Elovl4) protein play in the biosynthesis of essential fatty acids (FAs). Our results confirmed the Octopus vulgaris Scd is a ∆9 desaturase with relatively high affinity towards saturated FAs with ≥ C₁₈ chain lengths. Scd was unable to desaturate 20:1n-15 (^∆520:1) suggesting that its role in the biosynthesis of non-methylene interrupted FAs (NMI FAs) is limited to the introduction of the first unsaturation at ∆9 position. Interestingly, the previously characterised ∆5 fatty acyl desaturase was indeed able to convert 20:1n-9 (^∆1120:1) to ^∆5,1120:2, an NMI FA previously detected in octopus nephridium. Additionally, Elovl4 was able to mediate the production of 24:5n-3 and thus can contribute to docosahexaenoic acid (DHA) biosynthesis through the Sprecher pathway. Moreover, the octopus Elovl4 was confirmed to play a key role in the biosynthesis of very long-chain (>C₂₄) PUFAs. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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Open AccessArticle

Krill Oil-In-Water Emulsion Protects against Lipopolysaccharide-Induced Proinflammatory Activation of Macrophages In Vitro

by Gabriel A. Bonaterra, David Driscoll, Hans Schwarzbach and Ralf Kinscherf

Mar. Drugs 2017, 15(3), 74; https://doi.org/10.3390/md15030074 - 15 Mar 2017

Cited by 25 | Viewed by 5906

Abstract

Background: Parenteral nutrition is often a mandatory therapeutic strategy for cases of septicemia. Likewise, therapeutic application of anti-oxidants, anti-inflammatory therapy, and endotoxin lowering, by removal or inactivation, might be beneficial to ameliorate the systemic inflammatory response during the acute phases of critical illness. Concerning anti-inflammatory properties in this setting, omega-3 fatty acids of marine origin have been frequently described. This study investigated the anti-inflammatory and LPS-inactivating properties of krill oil (KO)-in-water emulsion in human macrophages in vitro. Materials and Methods: Differentiated THP-1 macrophages were activated using specific ultrapure-LPS that binds only on the toll-like receptor 4 (TLR4) in order to determine the inhibitory properties of the KO emulsion on the LPS-binding capacity, and the subsequent release of TNF-α. Results: KO emulsion inhibited the macrophage binding of LPS to the TLR4 by 50% (at 12.5 µg/mL) and 75% (at 25 µg/mL), whereas, at 50 µg/mL, completely abolished the LPS binding. Moreover, KO (12.5 µg/mL, 25 µg/mL, or 50 µg/mL) also inhibited (30%, 40%, or 75%, respectively) the TNF-α release after activation with 0.01 µg/mL LPS in comparison with LPS treatment alone. Conclusion: KO emulsion influences the LPS-induced pro-inflammatory activation of macrophages, possibly due to inactivation of the LPS binding capacity. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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2100 KiB

Open AccessFeature PaperArticle

Valorization of Lipids from Gracilaria sp. through Lipidomics and Decoding of Antiproliferative and Anti-Inflammatory Activity

by Elisabete Da Costa, Tânia Melo, Ana S. P. Moreira, Carina Bernardo, Luisa Helguero, Isabel Ferreira, Maria Teresa Cruz, Andreia M. Rego, Pedro Domingues, Ricardo Calado, Maria H. Abreu and Maria Rosário Domingues

Mar. Drugs 2017, 15(3), 62; https://doi.org/10.3390/md15030062 - 2 Mar 2017

Cited by 74 | Viewed by 8422

Abstract

The lipidome of the red seaweed Gracilaria sp., cultivated on land-based integrated multitrophic aquaculture (IMTA) system, was assessed for the first time using hydrophilic interaction liquid chromatography-mass spectrometry and tandem mass spectrometry (HILIC–MS and MS/MS). One hundred and forty-seven molecular species were identified in the lipidome of the Gracilaria genus and distributed between the glycolipids classes monogalactosyl diacylglyceride (MGDG), digalactosyl diacylglyceride (DGDG), sulfoquinovosyl monoacylglyceride (SQMG), sulfoquinovosyl diacylglyceride (SQDG), the phospholipids phosphatidylcholine (PC), lyso-PC, phosphatidylglycerol (PG), lyso-PG, phosphatidylinositol (PI), phosphatidylethanolamine (PE), phosphatic acid (PA), inositolphosphoceramide (IPC), and betaine lipids monoacylglyceryl- and diacylglyceryl-N,N,N-trimethyl homoserine (MGTS and DGTS). Antiproliferative and anti-inflammatory effects promoted by lipid extract of Gracilaria sp. were evaluated by monitoring cell viability in human cancer lines and by using murine macrophages, respectively. The lipid extract decreased cell viability of human T-47D breast cancer cells and of 5637 human bladder cancer cells (estimated half-maximal inhibitory concentration (IC₅₀) of 12.2 μg/mL and 12.9 μg/mL, respectively) and inhibited the production of nitric oxide (NO) evoked by the Toll-like receptor 4 agonist lipopolysaccharide (LPS) on the macrophage cell line RAW 264.7 (35% inhibition at a concentration of 100 μg/mL). These findings contribute to increase the ranking in the value-chain of Gracilaria sp. biomass cultivated under controlled conditions on IMTA systems. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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Review

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Open AccessReview

Marine Lipids on Cardiovascular Diseases and Other Chronic Diseases Induced by Diet: An Insight Provided by Proteomics and Lipidomics

by Lucía Méndez, Gabriel Dasilva, Nùria Taltavull, Marta Romeu and Isabel Medina

Mar. Drugs 2017, 15(8), 258; https://doi.org/10.3390/md15080258 - 18 Aug 2017

Cited by 16 | Viewed by 7229

Abstract

Marine lipids, especially ω-3 polyunsaturated fatty acids (PUFAs) eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), have largely been linked to prevention of diet-induced diseases. The anti-inflammatory and hypolipidemic properties of EPA and DHA supplementation have been well-described. However, there is still a significant lack of information about their particular mechanism of action. Furthermore, repeated meta-analyses have not shown conclusive results in support of their beneficial health effects. Modern “omics” approaches, namely proteomics and lipidomics, have made it possible to identify some of the mechanisms behind the benefits of marine lipids in the metabolic syndrome and related diseases, i.e., cardiovascular diseases and type 2 diabetes. Although until now their use has been scarce, these “omics” have brought new insights in this area of nutrition research. The purpose of the present review is to comprehensively show the research articles currently available in the literature which have specifically applied proteomics, lipidomics or both approaches to investigate the role of marine lipids intake in the prevention or palliation of these chronic pathologies related to diet. The methodology adopted, the class of marine lipids examined, the diet-related disease studied, and the main findings obtained in each investigation will be reviewed. Full article

(This article belongs to the Special Issue Marine Lipids 2017)

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