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.

Brown Algae (Phaeophyceae) from the Coast of Madagascar: preliminary Bioactivity Studies and Isolation of Natural Products

“…For example, Kim et al isolated four monogalactosyldiacylglycerols from the brown alga S. thunbergii collected at the coastal areas of Korea [ 32 ]. A series of monogalactosyldiacylglycerols has been identified by Liu and coworkers in Sargassum horneri [ 33 ]. 1- O -Palmitoyl-2- O -stearidonoyl-3- O -β-D-galactopyranosylglycerol ( 4 ) has been mentioned as a trace component in a mixture of monogalactolipids obtained from Scytonema sp.…”

Ethanol extract separated from Sargassum horneri (Turner) abate LPS-induced inflammation in RAW 264.7 macrophages

“…Side dishes or soup prepared by mixing S. horneri thallus with meat or fish are popular in the countries located in the East Asia region. In Japan, S. horneri is known as "akamoku" and is harvested at the maturation stage for eating in regions along the East Sea (Nomura et al 2012;Ma et al 2014).…”

One-Step Preparative Separation of Phytosterols from Edible Brown Seaweed Sargassum horneri by High-Speed Countercurrent Chromatography

“…S. horneri has been widely used as an edible alga and has various health benefits, such as protective role on bacteria, anti-proliferative effects on cancer cells, anti-inflammatory and antioxidant activity [3][4][5]. Due to the high content of polysaccharides, there are many studies on polysaccharides, and many achievements have been accomplished [6][7][8]. While, as another abundant compounds family present in S. horneri, the development of sterol-related health care products is relatively slow.…”