Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus
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 glycer...
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MDPI AG
2014-03-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/12/3/1406 |
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| author | Graciliana Lopes Georgios Daletos Peter Proksch Paula B. Andrade Patrícia Valentão |
| author_facet | Graciliana Lopes Georgios Daletos Peter Proksch Paula B. Andrade Patrícia Valentão |
| author_sort | Graciliana Lopes |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T06:58:44Z |
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| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-13T06:58:44Z |
| publishDate | 2014-03-01 |
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| series | Marine Drugs |
| spelling | doaj.art-3b4a7ce1c881459981896c64c8f4774f2022-12-22T02:57:11ZengMDPI AGMarine Drugs1660-33972014-03-011231406141810.3390/md12031406md12031406Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis LinnaeusGraciliana Lopes0Georgios Daletos1Peter Proksch2Paula B. Andrade3Patrícia Valentão4REQUIMTE/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, PortugalInstitute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, Universitätsstraße 1, Düsseldorf 40225, GermanyInstitute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University, Universitätsstraße 1, Düsseldorf 40225, GermanyREQUIMTE/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, PortugalREQUIMTE/Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, PortugalA 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.http://www.mdpi.com/1660-3397/12/3/1406Fucus spiralismonoacylglycerolmonogalactosyl diacylglycerolsanti-inflammatoryLC-MSNMR |
| spellingShingle | Graciliana Lopes Georgios Daletos Peter Proksch Paula B. Andrade Patrícia Valentão Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus Marine Drugs Fucus spiralis monoacylglycerol monogalactosyl diacylglycerols anti-inflammatory LC-MS NMR |
| title | Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus |
| title_full | Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus |
| title_fullStr | Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus |
| title_full_unstemmed | Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus |
| title_short | Anti-Inflammatory Potential of Monogalactosyl Diacylglycerols and a Monoacylglycerol from the Edible Brown Seaweed Fucus spiralis Linnaeus |
| title_sort | anti inflammatory potential of monogalactosyl diacylglycerols and a monoacylglycerol from the edible brown seaweed fucus spiralis linnaeus |
| topic | Fucus spiralis monoacylglycerol monogalactosyl diacylglycerols anti-inflammatory LC-MS NMR |
| url | http://www.mdpi.com/1660-3397/12/3/1406 |
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