marine drugs Books Marine Lipids 2017 Edited by Rosário Domingues, Ricardo Calado and Pedro Domingues Printed Edition of the Special Issue Published in Marine Drugs www.mdpi.com/journal/marinedrugs MDPI Marine Lipids 2017 Special Issue Editors Rosário Domingues Books Ricardo Calado Pedro Domingues MDPI • Basel • Beijing • Wuhan • Barcelona • Belgrade MDPI Special Issue Editors Rosário Domingues Ricardo Calado University of Aveiro University of Aveiro Portugal Portugal Pedro Domingues University of Aveiro Portugal Editorial Office MDPI AG St. Alban-Anlage 66 Basel, Switzerland This edition is a reprint of the Special Issue published online in the open access journal Marine Drugs (ISSN 1660-3397) in 2017 (available at: http://www.mdpi.com/journal/marinedrugs/special_issues/marine_lipids_2017). Books For citation purposes, cite each article independently as indicated on the article page online and as indicated below: Lastname, F.M.; Lastname, F.M. Article title. Journal Name Year, Article number, page range. First Edition 2018 ISBN 978-3-03842-799-5 (Pbk) ISBN 978-3-03842-800-8 (PDF) Articles in this volume are Open Access and distributed under the Creative Commons Attribution license (CC BY), which allows users to download, copy and build upon published articles even for commercial purposes, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. The book taken as a whole is © 2018 MDPI, Basel, Switzerland, distributed under the terms and conditions of the Creative Commons license CC BY-NC-ND (http://creativecommons.org/licenses/by-nc-nd/4.0/). MDPI Table of Contents About the Special Issue Editors ..................................... v Preface to ”Marine Lipids 2017”..................................... vii Elisabete da Costa, Tnia 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 Ros´arioDomingues Valorization of Lipids from Gracilaria sp. through Lipidomics and Decoding of Antiproliferative and Anti-Inflammatory Activity doi: 10.3390/md15030062 ....................................... 1 Gabriel A. Bonaterra, David Driscoll, Hans Schwarzbach and Ralf Kinscherf Krill Oil-In-Water Emulsion Protects against Lipopolysaccharide-Induced Proinflammatory Activation of Macrophages In Vitro doi: 10.3390/md15030074 ....................................... 18 Oscar´ Monroig, Rosa de Llanos, Inmaculada Var´o,Francisco Hontoria, Douglas R. Tocher, Sergi Puig and Juan C. Navarro 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 doi: 10.3390/md15030082 ....................................... 30 Books 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 An Extract from Shrimp Processing By-Products Protects SH-SY5Y Cells from Neurotoxicity β Induced by A 25–35 doi: 10.3390/md15030083 ....................................... 46 Kai-Min Yang and Po-Yuan Chiang Variation Quality and Kinetic Parameter of Commercial n-3 PUFA-Rich Oil during Oxidation via Rancimat doi: 10.3390/md15040097 ....................................... 65 Luc´ıaM´endez,Gabriel Dasilva, Nria Taltavull, Marta Romeu and Isabel Medina Marine Lipids on Cardiovascular Diseases and Other Chronic Diseases Induced by Diet: An Insight Provided by Proteomics and Lipidomics doi: 10.3390/md15080258 ....................................... 76 Phuc Nguyen Thien Le and Andrew P. Desbois Antibacterial Effect of Eicosapentaenoic Acid against Bacillus cereus and Staphylococcus aureus: Killing Kinetics, Selection for Resistance, and Potential Cellular Target doi: 10.3390/md15110334 .......................................105 S´onia 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 Lipophilic Fraction of Cultivated Bifurcaria bifurcata R. Ross: Detailed Composition and In Vitro Prospection of Current Challenging Bioactive Properties doi: 10.3390/md15110340 .......................................115 iii MDPI Alexander N. Shikov, Into Laakso, Olga N. Pozharitskaya, Tuulikki Sepp¨anen-Laakso, Anna S. Krishtopina, Marina N. Makarova, Heikki Vuorela and Valery Makarov Chemical Profiling and Bioactivity of Body Wall Lipids from Strongylocentrotus droebachiensis doi: 10.3390/md15120365 .......................................132 M. Barra, A. Llanos-Rivera, F. Cruzat, N. Pino-Maureira and R. R. Gonzlez-Sald´ıa The Marine Fungi Rhodotorula sp. (Strain CNYC4007) as a Potential Feed Source for Fish Larvae Nutrition doi: 10.3390/md15120369 .......................................143 Books iv MDPI Books MDPI Books MDPI Books MDPI Books MDPI marine drugs Article Valorization of Lipids from Gracilaria sp. through Lipidomics and Decoding of Antiproliferative and Anti-Inflammatory Activity Elisabete da Costa 1,Tânia Melo 1, Ana S. P. Moreira 1, Carina Bernardo 2, Luisa Helguero 2, Isabel Ferreira 3, Maria Teresa Cruz 3, Andreia M. Rego 4, Pedro Domingues 1, Ricardo Calado 5, Maria H. Abreu 4 and Maria Rosário Domingues 1,* 1 Centro de Espectrometria de Massa, Departamento de Química & QOPNA, Universidade de Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal; [email protected] (E.d.C.); [email protected] (T.M.); [email protected] (A.S.P.M.); [email protected] (P.D.) 2 Instituto de Biomedicina (IBIMED), Departamento de Ciências Médicas, Universidade de Aveiro, 3810-193 Aveiro, Portugal; [email protected] (C.B.); [email protected] (L.H.) 3 Centro de Neurociências e Biologia Celular (CNC), Universidade de Coimbra, 3004-517 Coimbra & Faculdade de Farmácia, Universidade de Coimbra, 3000-548 Coimbra, Portugal; [email protected] (I.F.); [email protected] (M.T.C.) 4 ALGAplus-Produção e Comercialização de Algas e seus Derivados, Lda., 3830-196 Ílhavo, Portugal; [email protected] (A.M.R.); [email protected] (M.H.A.) 5 Departamento de Biologia & CESAM, Universidade de Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal; [email protected] * Correspondence: [email protected] Books Academic Editor: Peer B. Jacobson Received: 11 November 2016; Accepted: 13 February 2017; Published: 2 March 2017 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 μ μ cancer cells (estimated half-maximal inhibitory concentration (IC50) of 12.2 g/mL and 12.9 g/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. Keywords: glycolipids; phospholipids; betaine lipids; seaweeds; bioactivity; mass spectrometry; hydrophilic interaction liquid chromatography–electrospray ionization–mass spectrometry HILIC–ESI–MS Mar. Drugs 2017, 15, 62 1 www.mdpi.com/journal/marinedrugs MDPI Mar. Drugs 2017, 15,62 1. Introduction Red seaweeds within the genus Gracilaria are one of the world’s most cultivated and valuable marine macrophytes. This group of seaweeds is well adapted to cultivation on land-based integrated multitrophic aquaculture (IMTA) systems, allowing its sustainable production under controlled and replicable conditions that provide a secure supply of high-grade seaweed biomass for demanding markets (e.g., food, pharmaceuticals) [1–3]. Gracilaria sp. is a source of multiple products, among which lipids, namely polyunsaturated fatty acids (PUFAs) such as arachidonic (20:4(n-6), AA) and eicosapentaenoic (20:5(n-6), EPA) acids, are emerging as valuable components [4]. Fatty acids (FAs) are mainly esterified to polar lipids such as glycolipids, phospholipids, and betaine lipids. Polar lipids are nowadays recognized as an important reservoir of fatty acids with nutritional value, e.g., n-3 FAs [5,6], and they are also considered high-value novel lipids with beneficial health effects such as antitumoral [7,8], antiviral [8,9], antifungal [10],