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Open AccessArticle

Anti-Inflammatory Activity of Glycolipids and a Polyunsaturated Fatty Acid Methyl Ester Isolated from the Marine Dinoflagellate Karenia mikimotoi

Center for Marine Science, University of North Carolina at Wilmington, 5600 Marvin K. Moss Lane, Wilmington, NC 28409, USA
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Mar. Drugs 2020, 18(3), 138; https://doi.org/10.3390/md18030138
Received: 15 January 2020 / Revised: 25 February 2020 / Accepted: 25 February 2020 / Published: 27 February 2020
A new monogalactosyldiacylglycerol (MGDG), a known monogalactosylmonoacylglycerol (MGMG) and a known polyunsaturated fatty acid methyl ester (PUFAME) were isolated from the marine dinoflagellate Karenia mikimotoi. The planar structure of the glycolipids was elucidated using mass spectroscopy (MS) and nuclear magnetic resonance (NMR) analyses and comparisons to the known glycolipid to confirm its structure. The MGDG was characterized as 3-O-β-D-galactopyranosyl-1-O-3,6,9,12,15-octadecapentaenoyl-2-O-tetradecanoylglycerol 1. The MGMG and PUFAME were characterized as (2S)-3-O-β-D-galactopyranosyl-1-O-3,6,9,12,15-octadecapentaenoylglycerol 2 and Methyl (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoate 3, respectively. The isolation of the PUFAME strongly supports the polyunsaturated fatty acid (PUFA) fragment of these glycolipids. The relative configuration of the sugar was deduced by comparisons of 3JHH values and proton chemical shifts with those of known glycolipids. All isolated compounds MGDG, MGMG and PUFAME 1-3 were evaluated for their antimicrobial and anti-inflammatory activity. All compounds modulated macrophage responses, with compound 3 exhibiting the greatest anti-inflammatory activity. View Full-Text
Keywords: dinoflagellate; Karenia mikimotoi; glycolipids; monogalactosyldiacylglycerol; monogalactosylmonoacylglycerol; polyunsaturated fatty acid methyl ester; Staphylococcus aureus; Escherichia coli; Candida albicans; anti-inflammatory activity dinoflagellate; Karenia mikimotoi; glycolipids; monogalactosyldiacylglycerol; monogalactosylmonoacylglycerol; polyunsaturated fatty acid methyl ester; Staphylococcus aureus; Escherichia coli; Candida albicans; anti-inflammatory activity
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Leutou, A.S.; McCall, J.R.; York, R.; Govindapur, R.R.; Bourdelais, A.J. Anti-Inflammatory Activity of Glycolipids and a Polyunsaturated Fatty Acid Methyl Ester Isolated from the Marine Dinoflagellate Karenia mikimotoi. Mar. Drugs 2020, 18, 138.

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