Oleic acid: An efficient inhibitor of glucosyltransferase

Fifteen species of wild edible mushrooms belonging to the genus Boletus (phylum Basidiomycota) were examined by high‐performance thin‐layer chromatographic (HP‐TLC) analysis and gas chromatography–mass spectrometry (GC‐MS) analysis for the presence of neutral, glyco‐, phospholipids, betaine lipids and fatty acids. The most abundant fatty acids were oleic acid (9‐18:1, 15–42%), linoleic acid (9,12‐18:2, 38–58%) and palmitic acid (16:0, 7–17%), but a great variation of the ester composition from one to another one was found. A comparison of neutral lipids, glycolipids, polar lipids and fatty acid composition of four species was done. Diacylglyceryltrimethylhomoserine and phosphatidylcholine were found as major components among polar lipids. Chemical constituents were characterized by GC‐MS, HP‐TLC and other chemical methods. Biologic activity of some isolated compounds from the genus Boletus is also discussed. PRACTICAL APPLICATIONS Mushrooms are important wildlife food in the Mediterranean countries. The lipids of mushrooms, sampled from the Upper Galilee, Golan Heights and Mount Carmel areas, and also from the forest around Jerusalem, were examined. The benefits of including fatty acids in the diets of humans are well documented. Fatty acids play a major role in the functioning of the immune system and the maintenance of all hormonal systems in the body. Mushrooms from the genus Boletus are an excellent source of both fatty acids and neutral and polar lipids. Boletus mushrooms are one of the most popular treats in Israeli houses.

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“…2002). It was recently shown that oleic acid is an efficient inhibitor of glucosyltransferase (Won et al. 2007).…”

Section: Resultsmentioning

confidence: 99%

LIPIDS AND FATTY ACIDS OF WILD EDIBLE MUSHROOMS OF THE GENUS BOLETUS

Hanŭs¹,

Shkrob²,

Dembitsky³

2008

Journal of Food Lipids

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“…Carbohydrate fatty esters had no effect on Gtf activity from S. sobrinus despite inhibiting growth of the organisms [Devulapalle et al, 2004]. In contrast, oleanic and oleic acid were efficient inhibitors of Gtf activity in solution [Kozai et al, 1987; Won et al, 2007]; the number of double bonds present along with free carboxyl groups was associated with inhibitory activity. According to Yanagida et al [2000], the high-molecular-weight plant polyphenols displaying strong anti-Gtf activity have a common structural feature shared with catechin-based oligomeric forms (condensed tannins) and/or gallate ester form compounds (hydrolyzable tannins).…”

Section: Inhibition Of Gtfsmentioning

confidence: 99%

Biology of <i>Streptococcus mutans-</i>Derived Glucosyltransferases: Role in Extracellular Matrix Formation of Cariogenic Biofilms

Bowen

Koo²

2011

Caries Res

867

1,016

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The importance of Streptococcus mutans in the etiology and pathogenesis of dental caries is certainly controversial, in part because excessive attention is paid to the numbers of S. mutans and acid production while the matrix within dental plaque has been neglected. S. mutans does not always dominate within plaque; many organisms are equally acidogenic and aciduric. It is also recognized that glucosyltransferases from S. mutans (Gtfs) play critical roles in the development of virulent dental plaque. Gtfs adsorb to enamel synthesizing glucans in situ, providing sites for avid colonization by microorganisms and an insoluble matrix for plaque. Gtfs also adsorb to surfaces of other oral microorganisms converting them to glucan producers. S. mutans expresses 3 genetically distinct Gtfs; each appears to play a different but overlapping role in the formation of virulent plaque. GtfC is adsorbed to enamel within pellicle whereas GtfB binds avidly to bacteria promoting tight cell clustering, and enhancing cohesion of plaque. GtfD forms a soluble, readily metabolizable polysaccharide and acts as a primer for GtfB. The behavior of soluble Gtfs does not mirror that observed with surface-adsorbed enzymes. Furthermore, the structure of polysaccharide matrix changes over time as a result of the action of mutanases and dextranases within plaque. Gtfs at distinct loci offer chemotherapeutic targets to prevent caries. Nevertheless, agents that inhibit Gtfs in solution frequently have a reduced or no effect on adsorbed enzymes. Clearly, conformational changes and reactions of Gtfs on surfaces are complex and modulate the pathogenesis of dental caries in situ, deserving further investigation.

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“…One focus for study of survival is the antimicrobial activity of long chain (typically C≥16) unsaturated free fatty acids that generate the acid mantle on skin [5], [6], [7], [8], [9]. These antimicrobial fatty acids (AFAs) are components of the innate immune system that function on skin and in abscesses [9], [10], [11], [12], [13], [14], [15], [16], [17], [18]. The amphipathic properties of AFAs are proposed to disrupt membrane function by altering permeability and fluidity and this is supported by transcriptional analyses of linoleic acid-treated S. aureus [6].…”

Section: Introductionmentioning

confidence: 99%

Mannitol Utilisation is Required for Protection of Staphylococcus aureus from Human Skin Antimicrobial Fatty Acids

et al. 2013

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Mannitol (Mtl) fermentation, with the subsequent production of acid, is a species signature of Staphylococcus aureus, and discriminates it from most other members of the genus. Inactivation of the gene mtlD, encoding Mtl-1-P dehydrogenase was found to markedly reduce survival in the presence of the antimicrobial fatty acid, linoleic acid. We demonstrate that the sugar alcohol has a potentiating action for this membrane-acting antimicrobial. Analysis of cellular metabolites revealed that, during exponential growth, the mtlD mutant accumulated high levels of Mtl and Mtl-P. The latter metabolite was not detected in its isogenic parent strain or a deletion mutant of the entire mtlABFD operon. In addition, the mtlD mutant strain exhibited a decreased MIC for H2O2, however virulence was unaffected in a model of septic arthritis.

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Oleic acid: An efficient inhibitor of glucosyltransferase

Cited by 38 publications

References 15 publications

LIPIDS AND FATTY ACIDS OF WILD EDIBLE MUSHROOMS OF THE GENUS BOLETUS

LIPIDS AND FATTY ACIDS OF WILD EDIBLE MUSHROOMS OF THE GENUS BOLETUS

Biology of <i>Streptococcus mutans-</i>Derived Glucosyltransferases: Role in Extracellular Matrix Formation of Cariogenic Biofilms

Mannitol Utilisation is Required for Protection of Staphylococcus aureus from Human Skin Antimicrobial Fatty Acids

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