Nonenzymatic α-Linolenic Acid Derivatives from the Sea: Macroalgae as Novel Sources of Phytoprostanes

被引:35
作者
Barbosa, Mariana [1 ]
Collado-Gonzalez, Jacinta [2 ]
Andrade, Paula B. [1 ]
Ferreres, Federico [2 ]
Valentao, Patricia [1 ]
Galano, Jean-Marie [3 ]
Durand, Thierry [3 ]
Gil-Izquierdo, Angel [2 ]
机构
[1] Univ Porto, Fac Farm, Dept Quim, Lab Farmacognosia,REQUIMTE LAQV, P-4050313 Oporto, Portugal
[2] CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, Murcia, Spain
[3] Univ Montpellier, CNRS, Fac Pharm, Inst Biomol Max Mousseron,ENSCM,UMR 5247, F-34059 Montpellier, France
关键词
alpha-linolenic acid; GC-MS; macroalgae; oxidized lipids; plytoprostanes; UHPLC-QqQ-MS/MS; POLYUNSATURATED FATTY-ACIDS; MARINE MACROALGAE; OXIDATIVE STRESS; OXYLIPINS; F-1; DEFENSE; METABOLITES; BIOACTIVES; OLIVE;
D O I
10.1021/acs.jafc.5b01904
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Phytoprostanes, autoxidation products of alpha-linolenic add, have been studied in several plant species, but information regarding the natural occurrence of this large family of biologically active oxidized lipids in macroalgae is still scarce. In this work, the free phytoprostane composition of 24 macroalgae species belonging to Chlorophyta, Phaeophyta, and Rhodophyta was determined through a recently validated UHPLC-QqQ-MS/MS method. The phytoprostane profiles varied greatly among all samples, F-1t-phytoprostanes and L-1-phytoprostanes being the predominant and minor classes, respectively. No correlation between the amounts of alpha-linolenic,acid in alga material and phytoprostane content was found. Therefore, it was hypothesized that the observed variability could be species-specific or result from interspecific interactions. This study provides new insight about the occurrence of phytoprostanes in macroalgae and opens doors, for future exploitation of these marine photosynthetic organisms as sources of potentially bioactive oxylipins, encouraging their incorporation in food products and nutraceutical and pharmaceutical preparations for human health.
引用
收藏
页码:6466 / 6474
页数:9
相关论文
共 43 条
[1]   Valuable compounds in macroalgae extracts [J].
Andrade, Paula B. ;
Barbosa, Mariana ;
Matos, Rui Pedro ;
Lopes, Graciliana ;
Vinholes, Juliana ;
Mouga, Teresa ;
Valentao, Patricia .
FOOD CHEMISTRY, 2013, 138 (2-3) :1819-1828
[2]   The effects of oxidation products of arachidonic acid and n3 fatty acids on vascular and platelet function [J].
Barden, Anne ;
Mas, Emilie ;
Henry, Peter ;
Durand, Thierry ;
Galano, Jean-Marie ;
Roberts, L. Jackson, II ;
Croft, Kevin D. ;
Mori, Trevor A. .
FREE RADICAL RESEARCH, 2011, 45 (04) :469-476
[3]   Flaxseed Oil Supplementation Increases Plasma F1-Phytoprostanes in Healthy Men [J].
Barden, Anne E. ;
Croft, Kevin D. ;
Durand, Thierry ;
Guy, Alexandre ;
Mueller, Martin J. ;
Mori, Trevor A. .
JOURNAL OF NUTRITION, 2009, 139 (10) :1890-1895
[4]   Cymatherelactone and cymatherols A-C, polycyclic oxylipins from the marine brown alga Cymathere triplicata [J].
Choi, Hyukjae ;
Proteau, Philip J. ;
Byrum, Tara ;
Gerwick, William H. .
PHYTOCHEMISTRY, 2012, 73 :134-141
[5]   Water Deficit during Pit Hardening Enhances Phytoprostanes Content, a Plant Biomarker of Oxidative Stress, in Extra Virgin Olive Oil [J].
Collado-Gonzalez, Jacinta ;
Perez-Lopez, David ;
Memmi, Houssem. ;
Carmen Gijon, M. ;
Medina, Sonia ;
Durand, Thierry ;
Guy, Alexandre ;
Galano, Jean-Marie ;
Ferreres, Federico ;
Torrecillas, Arturo ;
Gil-Izquierdo, Angel .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2015, 63 (14) :3784-3792
[6]   New UHPLC-QqQ-MS/MS method for quantitative and qualitative determination of free phytoprostanes in foodstuffs of commercial olive and sunflower oils [J].
Collado-Gonzalez, Jacinta ;
Medina, Sonia ;
Durand, Thierry ;
Guy, Alexandre ;
Galano, Jean-Marie ;
Torrecillas, Arturo ;
Ferreres, Federico ;
Gil-Izquierdo, Angel .
FOOD CHEMISTRY, 2015, 178 :212-220
[7]   New Bioactive Oxylipins Formed by Non-Enzymatic Free-Radical-Catalyzed Pathways: the Phytoprostanes [J].
Durand, Thierry ;
Bultel-Ponce, Valerie ;
Guy, Alexandre ;
Berger, Susanne ;
Mueller, Martin J. ;
Galano, Jean-Marie .
LIPIDS, 2009, 44 (10) :875-888
[8]   Total synthesis of the eight diastereomers of the syn-anti-syn phytoprostanes F1 types I and II [J].
El Fangour, S ;
Guy, A ;
Despres, V ;
Vidal, JP ;
Rossi, JC ;
Durand, T .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2498-2503
[9]   Total synthesis of phytoprostane F1 and its 16 epimer [J].
El Fangour, S ;
Guy, A ;
Vidal, JP ;
Rossi, JC ;
Durand, T .
TETRAHEDRON LETTERS, 2003, 44 (10) :2105-2108
[10]  
GERWICK WH, 1993, HYDROBIOLOGIA, V261, P653