Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus

Abstract

A monoacylglycerol (1) and a 1:1 mixture of two monogalactosyl diacylglycerols (MGDGs) (2 and 3) were isolated from the brown seaweed Fucus spiralis Linnaeus. The structures were elucidated by spectroscopic means (NMR and MS) and by comparison with the literature. Compound 1 was composed of a glycerol moiety linked to oleic acid (C18:1 Ω9). Compounds 2 and 3 contained a glycerol moiety linked to a galactose unit and eicosapentaenoic acid (C20:5 Ω3) combined with octadecatetraenoic acid (C18:4 Ω3) or linolenic acid (C18:3 Ω3), respectively. The isolated compounds were tested for their cytotoxic and anti-inflammatory activity in RAW 264.7 macrophage cells. All of them inhibited NO production at non-cytotoxic concentrations. The fraction consisting of compounds 2 and 3, in a ratio of 1:1, was slightly more effective than compound 1 (IC50 of 60.06 and 65.70 µg/mL, respectively). To our knowledge, this is the first report of these compounds from F. spiralis and on their anti-inflammatory capacity.

Isolates fromMonechma ciliatumseeds' extract hamperedPorphyromonas gingivalishemagglutinins

“…Furthermore, we found other two compounds claasified into diacylglycerols (1,2‐dioleylglycerol, and 1,3‐dioleylglycerol) from M. ciliatum . These compounds, which exist in several vegetable and seed oil, are well known for their functional roles in medicinal fields (AlAttas, Zahran, & Turkistany, ; Huang, Altimova, Myers, & Ebersole, ; Lopes, Daletos, Proksch, Andrade, & Valentão, ). However, and to the best of our knowledge, these compounds are very rare in higher plants.…”

Fatty acids from edible sea hares: anti-inflammatory capacity in LPS-stimulated RAW 264.7 cells involves iNOS modulation

“…4 u-3-PUFA act by decreasing the production of inammatory eicosanoids, cytokines and nitric oxide. 36 The monogalactosyl diacylglycerols containing u-3 fatty acids in their structure were more effective than the monoacylglycerol containing oleic acid, a u-9 fatty acid. 35 The Aplysia extracts studied herein contained signicant amounts of these three u-3 fatty acids (203.17 and 288.30 mg kg À1 , dry weight, in A. fasciata and A. punctata, respectively, Table 1), which should contribute to the overall effects.…”

“…Concerning to the last, it has been previously shown that the expression of iNOS was inhibited by EPA, DHA 33 and also a-linolenic acid. 36 So, u-3 fatty acids, not only in the free form, but also in complex molecules, appear to contribute most to the anti-inammatory activity. The presence of higher amounts of u-3 fatty acids in A. punctata is accompanied by the presence of higher amounts of the pro-inammatory fatty acid cis-5,8,11,14-eicosatetraenoic (arachidonic acid) and the balance between the compounds can impart similar effects on cNO of A. punctata and A. fasciata extracts.…”

Valorization of Lipids from Gracilaria sp. through Lipidomics and Decoding of Antiproliferative and Anti-Inflammatory Activity

“…Some studies reported that polar lipids isolated from seaweeds can promote growth-inhibiting effects on human hepatocellular carcinoma cell lines (HepG2) [16] and thus can act as inhibitors of DNA polymerases with capability to inhibit tumor cell proliferation [17]. Moreover, they have been associated with anti-inflammatory properties through the inhibition of pro-inflammatory cytokines interleukin IL-6 and IL-8 production [15] and/or by the inhibition of nitric oxide (NO) production [18,19,20,21]. Lipid-based agents are therefore emerging molecules in therapeutics aimed to regulate inflammatory pathways or even impair downstream tumorigenic processes [22,23,24].…”