title: Isolation of the molecular species of monogalactosyldiacylglycerols from brown edible seaweed Sargassum horneri and their inhibitory effects on triglyceride accumulation in 3T3-L1 adipocytes.
abstract: The chemical composition of monogalactosyldiacylglycerols (MGDGs) from brown alga Sargassum horneri and their inhibitory effects on lipid accumulation were investigated in this study. A total of 10 molecular species of MGDGs were identified using nuclear magnetic resonance, alkaline hydrolysis, gas chromatography-flame ionization detector, and high-performance liquid chromatography-tandem mass spectrometry methods. Individual molecular species of MGDGs, including (2S)-1-O-myristoyl-2-O-palmitoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol (1), (2S)-1-O-myristoyl-2-O-linoleyl-3-O-β-D-galactopyranosyl-sn-glycerol (3), (2S)-1-O-palmitoyl-2-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol (5), (2S)-1-O-myristoyl-2-O-oleyl-3-O-β-D-galactopyranosyl-sn-glycerol (7), (2S)-1-O-palmitoyl-2-O-palmitoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol (8), (2S)-1-O-palmitoyl-2-O-linoleyl-3-O-β-D-galactopyranosyl-sn-glycerol (9), and (2S)-1-O-palmitoyl-2-O-oleyl-3-O-β-D-galactopyranosyl-sn-glycerol (10), were then furnished using semi-preparative high-performance liquid chromatography, and their inhibitory effects on triglyceride (TG) accumulation and free fatty acid (FFA) levels in 3T3-L1 adipocytes were evaluated. Compounds 3 and 9 showed inhibitory effects on TG and FFA accumulation, with TG levels of 1.568 ± 0.2808 and 1.701 ± 0.1460 μmol/L and FFA levels of 0.149 ± 0.0258 and 0.198 ± 0.0229 mequiv/L, respectively, which were more effective than other compounds. The primary structure-activity relationship suggested that linoleyl [18:2(ω-6)] in the sn-2 position played an important role on triglyceride accumulation inhibition.
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, Institute of Marine Foods and Drugs, Ocean University of China , Qingdao, Shandong 266003, People's Republic of China.
authors.forename: Ai-Cui
authors.initials: AC
authors.lastname: Ma
authors.forename: Zhen
authors.initials: Z
authors.lastname: Chen
authors.forename: Tao
authors.initials: T
authors.lastname: Wang
authors.forename: Ni
authors.initials: N
authors.lastname: Song
authors.forename: Qian
authors.initials: Q
authors.lastname: Yan
authors.forename: Yu-Chun
authors.initials: YC
authors.lastname: Fang
authors.forename: Hua-Shi
authors.initials: HS
authors.lastname: Guan
authors.forename: Hong-Bing
authors.initials: HB
authors.lastname: Liu
mesh_terms: D016475:3T3 Cells; D017667:Adipocytes / Q000187:drug effects* / Q000378:metabolism; D000818:Animals; D038983:Galactolipids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013058:Mass Spectrometry; D051379:Mice; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D044647:Sargassum / Q000737:chemistry*; D012624:Seaweed / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014280:Triglycerides / Q000378:metabolism*; D014675:Vegetables / Q000737:chemistry
chemical_list: D038983:Galactolipids; D010936:Plant Extracts; D014280:Triglycerides; C009909:monogalactosyldiacylglycerol
keywords: 3T3-L1 adipocytes; Sargassum horneri; monogalactosyldiacylglycerols; triglyceride accumulation inhibition