Abstract
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.
Highlights
Microorganisms isolated from marine environments have been considered as a good source for exploration of novel natural products [1,2]
This functional response is in agreement with the flow cytometry data (Figure 4), where compound 3 had the most effects on macrophage expression of activation markers and size/complexity
Compounds were tested for antimicrobial activity using a Minimum Inhibitory Concentration (MIC) assay with the gram-positive bacteria Staphylococcus aureus, the gram-negative bacteria Escherichia coli, and the fungi Candida albicans (Carolina Biological, Greensboro, NC, USA)
Summary
Microorganisms isolated from marine environments have been considered as a good source for exploration of novel natural products [1,2]. Has been found that the peridinin-containing dinoflagellates cholorplast membranes are composed principally of two galactolipids, mono‐and be divided into two clusters depending on whether the major forms of MGDG and DGDG are C18/C18 digalactosyldiacylglycerol. 18:5n-3 orthe eicosapentaenoic containing dinoflagellates can be divided into two clusters depending on whether the major of acid 20:5n-3 [23] Fatty acids such as 18:5n-3 and 14:0 are found to be key components offorms the MGDGs. MGDG and DGDG are C18/C18 (sn‐1/sn‐2 regiochemistry) or C20/C18 containing octadecatetraenoic and MGMGs in the dinoflagellate Karenia brevis. Lepidodinium chlorophorum, was acid 18:5n‐3 or eicosapentaenoic acid 20:5n‐3 [23] Fatty acids such as 18:5n‐3 and 14:0 are found to found to possess glycoglycerolipids with fatty acid (FA) containing side chains of 18:5/16:4, 18:5/18:5 be key components of the MGDGs and MGMGs in the dinoflagellate Karenia brevis.
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