{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,12]],"date-time":"2026-05-12T19:21:21Z","timestamp":1778613681377,"version":"3.51.4"},"reference-count":65,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2017,3,2]],"date-time":"2017-03-02T00:00:00Z","timestamp":1488412800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"to Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT, Portugal), European Union, QREN, POPH, FEDER and COMPETE","award":["project PEst-C\/QUI\/UI0062\/2011"],"award-info":[{"award-number":["project PEst-C\/QUI\/UI0062\/2011"]}]},{"name":"RNEM","award":["REDE\/1504\/REM\/2005"],"award-info":[{"award-number":["REDE\/1504\/REM\/2005"]}]},{"DOI":"10.13039\/100013239","name":"CESAM","doi-asserted-by":"publisher","award":["UID\/AMB\/50017\/2013"],"award-info":[{"award-number":["UID\/AMB\/50017\/2013"]}],"id":[{"id":"10.13039\/100013239","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>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\u2013MS 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 \u03bcg\/mL and 12.9 \u03bcg\/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 \u03bcg\/mL). These findings contribute to increase the ranking in the value-chain of Gracilaria sp. biomass cultivated under controlled conditions on IMTA systems.<\/jats:p>","DOI":"10.3390\/md15030062","type":"journal-article","created":{"date-parts":[[2017,3,2]],"date-time":"2017-03-02T10:31:17Z","timestamp":1488450677000},"page":"62","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":78,"title":["Valorization of Lipids from Gracilaria sp. through Lipidomics and Decoding of Antiproliferative and Anti-Inflammatory Activity"],"prefix":"10.3390","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0309-5132","authenticated-orcid":false,"given":"Elisabete","family":"Da Costa","sequence":"first","affiliation":[{"name":"Centro de Espectrometria de Massa, Departamento de Qu\u00edmica &amp; QOPNA, Universidade de Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"}]},{"given":"T\u00e2nia","family":"Melo","sequence":"additional","affiliation":[{"name":"Centro de Espectrometria de Massa, Departamento de Qu\u00edmica &amp; QOPNA, Universidade de Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"}]},{"given":"Ana","family":"Moreira","sequence":"additional","affiliation":[{"name":"Centro de Espectrometria de Massa, Departamento de Qu\u00edmica &amp; QOPNA, Universidade de Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"}]},{"given":"Carina","family":"Bernardo","sequence":"additional","affiliation":[{"name":"Instituto de Biomedicina (IBIMED), Departamento de Ci\u00eancias M\u00e9dicas, Universidade de Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8237-2390","authenticated-orcid":false,"given":"Luisa","family":"Helguero","sequence":"additional","affiliation":[{"name":"Instituto de Biomedicina (IBIMED), Departamento de Ci\u00eancias M\u00e9dicas, Universidade de Aveiro, 3810-193 Aveiro, Portugal"}]},{"given":"Isabel","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Centro de Neuroci\u00eancias e Biologia Celular (CNC), Universidade de Coimbra, 3004-517 Coimbra &amp; Faculdade de Farm\u00e1cia, Universidade de Coimbra, 3000-548 Coimbra, Portugal"}]},{"given":"Maria","family":"Cruz","sequence":"additional","affiliation":[{"name":"Centro de Neuroci\u00eancias e Biologia Celular (CNC), Universidade de Coimbra, 3004-517 Coimbra &amp; Faculdade de Farm\u00e1cia, Universidade de Coimbra, 3000-548 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5632-423X","authenticated-orcid":false,"given":"Andreia","family":"Rego","sequence":"additional","affiliation":[{"name":"ALGAplus-Produ\u00e7\u00e3o e Comercializa\u00e7\u00e3o de Algas e seus Derivados, Lda., 3830-196 \u00cdlhavo, Portugal"}]},{"given":"Pedro","family":"Domingues","sequence":"additional","affiliation":[{"name":"Centro de Espectrometria de Massa, Departamento de Qu\u00edmica &amp; QOPNA, Universidade de Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"}]},{"given":"Ricardo","family":"Calado","sequence":"additional","affiliation":[{"name":"Departamento de Biologia &amp; CESAM, Universidade de Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"}]},{"given":"Maria","family":"Abreu","sequence":"additional","affiliation":[{"name":"ALGAplus-Produ\u00e7\u00e3o e Comercializa\u00e7\u00e3o de Algas e seus Derivados, Lda., 3830-196 \u00cdlhavo, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5357-3601","authenticated-orcid":false,"given":"Maria","family":"Domingues","sequence":"additional","affiliation":[{"name":"Centro de Espectrometria de Massa, Departamento de Qu\u00edmica &amp; QOPNA, Universidade de Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,3,2]]},"reference":[{"key":"ref_1","unstructured":"Pereira, L., and Magalhaes, J. (2014). Marine Algae: Biodiversity, Taxonomy, Environmental Assessment, and Biotechnology, CRC Press."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.aquaculture.2010.12.036","article-title":"IMTA with Gracilaria vermiculophylla: Productivity and nutrient removal performance of the seaweed in a land-based pilot scale system","volume":"312","author":"Abreu","year":"2011","journal-title":"Aquaculture"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Leal, M.C., Rocha, R.J.M., Rosa, R., and Calado, R. (2016). Aquaculture of marine non-food organisms: What, why and how?. Rev. Aquac., 1\u201324.","DOI":"10.1111\/raq.12168"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3754","DOI":"10.3390\/md11103754","article-title":"The red seaweed Gracilaria gracilis as a multi products source","volume":"11","author":"Francavilla","year":"2013","journal-title":"Mar. Drugs"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1016\/j.plipres.2006.01.001","article-title":"Lipids and lipid metabolism in eukaryotic algae","volume":"45","author":"Guschina","year":"2006","journal-title":"Prog. Lipid Res."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1186\/1476-511X-10-104","article-title":"Polyunsaturated fatty acids in various macroalgal species from North Atlantic and tropical seas","volume":"10","author":"Helsper","year":"2011","journal-title":"Lipids Health Dis."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"483","DOI":"10.1016\/j.biotechadv.2011.05.016","article-title":"Algal chemodiversity and bioactivity: Sources of natural variability and implications for commercial application","volume":"29","author":"Stengel","year":"2011","journal-title":"Biotechnol. Adv."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.tifs.2011.09.001","article-title":"Seaweeds: A sustainable functional food for complementary and alternative therapy","volume":"23","author":"Mohamed","year":"2012","journal-title":"Trends Food Sci. Technol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"4628","DOI":"10.3390\/md11114628","article-title":"Antiviral sulfoquinovosyldiacylglycerols (SQDGs) from the Brazilian brown seaweed Sargassum vulgare","volume":"11","author":"Sassaki","year":"2013","journal-title":"Mar. Drugs"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"244","DOI":"10.1590\/S0102-695X2011005000056","article-title":"Glycolipids from macroalgae: Potential biomolecules for marine biotechnology?","volume":"21","author":"Mattos","year":"2011","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_11","first-page":"1","article-title":"Glycolipids from seaweeds and their potential biotechnological applications","volume":"4","author":"Pereira","year":"2014","journal-title":"Front. Cell. Infect. Microbiol."},{"key":"ref_12","first-page":"1","article-title":"Health effects of dietary phospholipids","volume":"11","author":"Taylor","year":"2012","journal-title":"Lipids Health Dis."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Da Costa, E., Silva, J., Mendon\u00e7a, S., Abreu, M., and Domingues, M. (2016). Lipidomic approaches towards deciphering glycolipids from microalgae as a reservoir of bioactive lipids. Mar. Drugs, 14.","DOI":"10.3390\/md14050101"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Maciel, E., Leal, M.C., Lilleb\u00f8, A.I., Domingues, P., Domingues, M.R., and Calado, R. (2016). Bioprospecting of marine macrophytes using MS-based lipidomics as a new approach. Mar. Drugs, 14.","DOI":"10.3390\/md14030049"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"5402","DOI":"10.3390\/md13085402","article-title":"The Anti-Inflammatory effect of algae-derived lipid extracts on lipopolysaccharide (LPS)-stimulated human THP-1 macrophages","volume":"13","author":"Robertson","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_16","first-page":"8404","article-title":"Identification of sulfoglycolipid bioactivities and characteristic fatty acids of marine macroalgae","volume":"60","author":"Tsai","year":"2012","journal-title":"JAFC"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"684","DOI":"10.1248\/cpb.46.684","article-title":"Sulfoquinovosyldiacylglycerol, KM043, a new potent inhibitor of eukaryotic DNA polymerases and HIV-reverse transcriptase type 1 from a marine red alga, Gigartina tenella","volume":"46","author":"Ohta","year":"1998","journal-title":"Chem. Pharm. Bull."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6227","DOI":"10.1021\/jf020290y","article-title":"In vitro anti-inflammatory and anti-proliferative activity of sulfolipids from the red alga Porphyridium cruentum","volume":"50","author":"Debiton","year":"2002","journal-title":"J. Agric. Food Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1406","DOI":"10.3390\/md12031406","article-title":"Anti-inflammatory potential of monogalactosyl diacylglycerols and a monoacylglycerol from the edible brown seaweed Fucus spiralis Linnaeus","volume":"12","author":"Lopes","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/j.phytochem.2014.02.004","article-title":"Polar lipids from the marine macroalgae Palmaria palmata inhibit lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophage cells","volume":"101","author":"Banskota","year":"2014","journal-title":"Phytochemistry"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1565","DOI":"10.1007\/s10811-013-0174-5","article-title":"Lipids isolated from the cultivated red alga Chondrus crispus inhibit nitric oxide production","volume":"26","author":"Banskota","year":"2014","journal-title":"J. Appl. Phycol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"216","DOI":"10.1080\/01635580701277908","article-title":"Anti-tumor effects of the glycolipids fraction from spinach which inhibited DNA polymerase activity","volume":"57","author":"Maeda","year":"2007","journal-title":"Nutr. Cancer"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1016\/j.cbpc.2010.08.008","article-title":"Marine pharmacology in 2007\u20132008: Marine compounds with antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the immune and nervous system, and other miscellaneous mec","volume":"153","author":"Mayer","year":"2011","journal-title":"Comp. Biochem. Physiol. C Toxicol. Pharmacol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1920","DOI":"10.3390\/md10091920","article-title":"Polyunsaturated fatty acids of marine macroalgae: Potential for nutritional and pharmaceutical applications","volume":"10","author":"Pereira","year":"2012","journal-title":"Mar. Drugs"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1016\/j.algal.2015.09.020","article-title":"Decoding bioactive polar lipid profile of the macroalgae Codium tomentosum from a sustainable IMTA system using a lipidomic approach","volume":"12","author":"Melo","year":"2015","journal-title":"Algal Res."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1016\/j.algal.2015.02.016","article-title":"Lipidomics as a new approach for the bioprospecting of marine macroalgae-Unraveling the polar lipid and fatty acid composition of Chondrus crispus","volume":"8","author":"Melo","year":"2015","journal-title":"Algal Res."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1125","DOI":"10.1016\/S0305-1978(03)00043-7","article-title":"Variability of the fatty acids of the marine green algae belonging to the genus Codium","volume":"31","author":"Dembitsky","year":"2003","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1515\/BOT.2002.003","article-title":"Fatty acids of marine algae from the Pacific Coast of North California","volume":"45","author":"Khotimchenko","year":"2002","journal-title":"Bot. Mar."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"932","DOI":"10.1016\/j.foodchem.2013.08.130","article-title":"Characterisation of lipid fraction of marine macroalgae by means of chromatography techniques coupled to mass spectrometry","volume":"145","author":"Ragonese","year":"2014","journal-title":"Food Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"186","DOI":"10.1023\/A:1020471709232","article-title":"Distribution of glyceroglycolipids in marine algae and grasses","volume":"38","author":"Khotimchenko","year":"2002","journal-title":"Chem. Nat. Compd."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1007\/s10600-005-0130-y","article-title":"Lipids from marine alga Gracilaria verrucosa","volume":"41","author":"Khotimchenko","year":"2005","journal-title":"Chem. Nat. Compd."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"721","DOI":"10.1016\/j.phytochem.2004.01.013","article-title":"Fatty acid composition of individual polar lipid classes from marine macrophytes","volume":"65","author":"Sanina","year":"2004","journal-title":"Phytochemistry"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1007\/s10811-012-9876-3","article-title":"Seasonal composition of lipids, fatty acids, and sterols in the edible red alga Grateloupia turuturu","volume":"25","author":"Kendel","year":"2013","journal-title":"J. Appl. Phycol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"4770","DOI":"10.1021\/ef201061j","article-title":"Algae polar lipids characterized by online liquid chromatography coupled with hybrid linear quadrupole ion trap\/fourier transform ion cyclotron resonance mass spectrometry","volume":"25","author":"He","year":"2011","journal-title":"Energy Fuels"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3185","DOI":"10.1002\/rcm.3190","article-title":"Identification of sulfoglycolipids from the alga Porphyridium purpureum by matrix-assisted laser desorption\/ionisation quadrupole ion trap time-of-flight mass spectrometry","volume":"21","author":"Naumann","year":"2007","journal-title":"Rappid Commun. Mass Spectrom."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1007\/s11306-011-0318-z","article-title":"Plant lipidomicss based on hydrophilic interaction chromatography coupled to ion trap time-of flight mass spectrometry","volume":"9","author":"Okazaki","year":"2011","journal-title":"Metabolomics."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1093\/pcp\/pct156","article-title":"Nitrate and phosphate regimes induced lipidomic and biochemical changes in the intertidal macroalga Ulva lactuca (Ulvophyceae, Chlorophyta)","volume":"55","author":"Kumari","year":"2014","journal-title":"Plant Cell Physiol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1007\/s11745-012-3748-0","article-title":"Molecular ion-independent quantification of polar glycerolipid classes in marine plankton using triple quadrupole MS","volume":"48","author":"Popendorf","year":"2013","journal-title":"Lipids"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1380","DOI":"10.1039\/c3np70057g","article-title":"Biogeography and biodiscovery hotspots of macroalgal marine natural products","volume":"30","author":"Leal","year":"2013","journal-title":"Nat. Prod. Rep."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"3295","DOI":"10.1016\/0031-9422(89)80334-6","article-title":"Alterations in lipid metabolism caused by illumination of the marine red algae Chondrus crispus and Polysiphonia lanosa","volume":"28","author":"Pettitt","year":"1989","journal-title":"Phytochemistry"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1016\/0031-9422(89)80020-2","article-title":"Lipids of the marine red algae, Chondrus crispus and Polysiphonia lanosa","volume":"28","author":"Trevor","year":"1989","journal-title":"Phytochemistry"},{"key":"ref_42","first-page":"1","article-title":"Lipid metabolism in the red marine algae Chondrus Crispus and Polysinphonza Lanosa as modified by temperature","volume":"28","author":"Harwood","year":"1989","journal-title":"Phytochemistry"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"918","DOI":"10.3390\/md10040918","article-title":"Structural characterization and anti-HSV-1 and HSV-2 activity of glycolipids from the marine algae Osmundaria obtusiloba isolated from Southeastern Brazilian coast","volume":"10","author":"Sassaki","year":"2012","journal-title":"Mar. Drugs"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1023\/B:RUBI.0000023103.14189.27","article-title":"An inositol-containing sphingolipid from the red alga Gracilaria verrucosa","volume":"30","author":"Khotimchenko","year":"2004","journal-title":"Russ. J. Bioorg. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1007\/BF02489414","article-title":"Betaine Lipids","volume":"1","author":"Sato","year":"1992","journal-title":"Bot. Mag."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/0163-7827(95)00009-7","article-title":"Betaine ether-linked glycerolipids","volume":"35","author":"Dembitsky","year":"1996","journal-title":"Prog. Lipid Res."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1515\/BOT.2006.004","article-title":"Variations in lipid composition among different developmental stages of Gracilaria verrucosa (Rhodophyta)","volume":"49","author":"Khotimchenko","year":"2006","journal-title":"Bot. Mar."},{"key":"ref_48","unstructured":"(2003). Diet, Nutrition and the Prevention of Chronic Diseases, World Health Organization. Available online: http:\/\/www.who.int\/dietphysicalactivity\/publications\/trs916\/en\/."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"674","DOI":"10.3181\/0711-MR-311","article-title":"The importance of the omega-6\/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases","volume":"233","author":"Simopoulos","year":"2008","journal-title":"Exp. Biol. Med."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1016\/S0753-3322(02)00253-6","article-title":"The importance of the ratio of omega-6\/omega-3 essential fatty acids","volume":"56","author":"Simopoulos","year":"2002","journal-title":"Biomed. Pharmacother."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1016\/j.medici.2016.05.003","article-title":"The importance of n-6\/n-3 fatty acids ratio in the major depressive disorder","volume":"52","author":"Husted","year":"2016","journal-title":"Medicina"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1016\/j.pharmthera.2015.01.008","article-title":"Anti-tumor activities of lipids and lipid analogues and their development as potential anticancer drugs","volume":"150","author":"Murray","year":"2015","journal-title":"Pharmacol. Ther."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"154","DOI":"10.1290\/0409058.1","article-title":"Growth inhibition and induction of differentiation and apoptosis mediated by sodium butyrate in Caco-2 cells with algal glycolipids","volume":"41","author":"Hossain","year":"2005","journal-title":"In Vitro Cell. Dev. Biol. Anim."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3634","DOI":"10.3390\/md12063634","article-title":"Total synthesis and structure-activity relationship of glycoglycerolipids from marine organisms","volume":"12","author":"Zhang","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"15401","DOI":"10.3390\/ijms131115401","article-title":"Marine omega-3 phospholipids: Metabolism and biological activities","volume":"13","author":"Burri","year":"2012","journal-title":"Int. J. Mol. Sci."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1354","DOI":"10.3390\/molecules15031354","article-title":"Synthesis of lysophospholipids","volume":"15","author":"Servi","year":"2010","journal-title":"Molecules"},{"key":"ref_57","first-page":"37","article-title":"Monogalactosyldiacylglycerols, potent nitric oxide inhibitors from the marine microalga Tetraselmis chui","volume":"27","author":"Banskota","year":"2012","journal-title":"Nat. Prod. Res."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4212","DOI":"10.1128\/jb.173.13.4212-4219.1991","article-title":"Hydrocarbon assimilation and biosurfactant production in Pseudomonas aeruginosa mutants","volume":"173","author":"Koch","year":"1991","journal-title":"J. Bacteriol."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1007\/s10549-011-1823-5","article-title":"Lipidomic approach to identify patterns in phospholipid profiles and define class differences in mammary epithelial and breast cancer cells","volume":"133","author":"Cotrim","year":"2012","journal-title":"Breast Cancer Res. Treat."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1016\/0003-2697(70)90343-X","article-title":"Spectrophotometric determination of phosphate esters in the presence and absence of orthophosphate","volume":"36","author":"Bartlett","year":"1970","journal-title":"Anal. Biochem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1016\/j.chroma.2006.10.022","article-title":"Simultaneous analysis of glycolipids and phospholids molecular species in avocado (Persea americana Mill) fruit","volume":"1150","author":"Pacetti","year":"2007","journal-title":"J. Chromatogr. A"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1002\/jms.3129","article-title":"Photooxidation of glycated and non-glycated phosphatidylethanolamines monitored by mass spectrometry","volume":"48","author":"Melo","year":"2013","journal-title":"J. Mass Spectrom."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"457","DOI":"10.1002\/jcp.24152","article-title":"Lipidomic analysis of phospholipids from human mammary epithelial and breast cancer cell lines","volume":"228","author":"Cotrim","year":"2013","journal-title":"J. Cell. Physiol."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"5421","DOI":"10.1046\/j.1432-1327.2000.01606.x","article-title":"Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity","volume":"267","author":"Wilson","year":"2000","journal-title":"Eur. J. Biochem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/0003-2697(82)90118-X","article-title":"Analysis of nitrate, nitrite, and 15N nitrate in biological fluids","volume":"126","author":"Green","year":"1982","journal-title":"Anal. 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