Journal articles: '3-hydroxy fatty acids'

1

Wood, Paul L. "Fatty Acyl Esters of Hydroxy Fatty Acid (FAHFA) Lipid Families." Metabolites 10, no. 12 (December 17, 2020): 512. http://dx.doi.org/10.3390/metabo10120512.

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Fatty Acyl esters of Hydroxy Fatty Acids (FAHFA) encompass three different lipid families which have incorrectly been classified as wax esters. These families include (i) Branched-chain FAHFAs, involved in the regulation of glucose metabolism and inflammation, with acylation of an internal branched-chain hydroxy-palmitic or -stearic acid; (ii) ω-FAHFAs, which function as biosurfactants in a number of biofluids, are formed via acylation of the ω-hydroxyl group of very-long-chain fatty acids (these lipids have also been designated as o-acyl hydroxy fatty acids; OAHFA); and (iii) Ornithine-FAHFAs are bacterial lipids formed by the acylation of short-chain 3-hydroxy fatty acids and the addition of ornithine to the free carboxy group of the hydroxy fatty acid. The differences in biosynthetic pathways and cellular functions of these lipid families will be reviewed and compared to wax esters, which are formed by the acylation of a fatty alcohol, not a hydroxy fatty acid. In summary, FAHFA lipid families are both unique and complex in their biosynthesis and their biological actions. We have only evaluated the tip of the iceberg and much more exciting research is required to understand these lipids in health and disease.

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Nichols, Frank, and Baliram Maraj. "Relationship between Hydroxy Fatty Acids and Prostaglandin E2 in Gingival Tissue." Infection and Immunity 66, no. 12 (December 1, 1998): 5805–11. http://dx.doi.org/10.1128/iai.66.12.5805-5811.1998.

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ABSTRACT Bacterial hydroxy fatty acids and alpha-hydroxy fatty acids have been demonstrated in complex lipid extracts of subgingival plaque and gingival tissue. However, little is known about the relationship between these hydroxy fatty acids in plaque and gingival tissues or the significance of these complex lipids in promoting inflammatory periodontal disease. The present study determined the percentages of ester-linked and amide-linked hydroxy fatty acids in complex lipids recovered from plaque and gingival tissue samples and the relationship between bacterial hydroxy fatty acids and alpha-hydroxy fatty acids in the lipid extracts. To evaluate a potential role for these hydroxy fatty acids in inflammatory periodontal disease, gingival tissue samples were examined for a relationship between prostaglandin E2 (PGE2) and hydroxy fatty acids recovered in gingival lipid. This investigation demonstrated that alpha-hydroxy fatty acids are only ester linked in plaque lipids but are largely amide linked in gingival tissue lipids. Furthermore, the level of alpha-hydroxy fatty acid in gingival lipid is directly related to the level of the bacterial hydroxy fatty acid 3-OHiso-branched C17:0 (3-OH iC17:0) in the same lipid extract. However, the relationship between hydroxy fatty acids in gingival lipids does not parallel the fatty acid relationship observed in plaque lipids. Finally, alpha-hydroxy fatty acid levels in gingival tissue lipids correlate directly with the recovery of PGE2 in the same tissue samples. These results demonstrate that alpha-hydroxy fatty acid levels in gingival lipids are directly related to both 3-OH iC17:0 bacterial lipid levels and PGE2 levels. These results indicate that in periodontal tissues there are unusual host-parasite interactions involving penetration of bacterial lipid in association with an altered gingival lipid metabolism and prostaglandin synthesis.

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Yang, Nian-Yun, Yi-Fang Yang, and Kun Li. "Analysis of Hydroxy Fatty Acids from the Pollen of Brassica campestris L. var. oleifera DC. by UPLC-MS/MS." Journal of Pharmaceutics 2013 (October 10, 2013): 1–6. http://dx.doi.org/10.1155/2013/874875.

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Ultraperformance liquid chromatography coupled with negative electrospray tandem mass spectrometry (UPLC-ESI-MS/MS) was used to determine 7 hydroxy fatty acids in the pollen of Brassica campestris L. var. oleifera DC. All the investigated hydroxy fatty acids showed strong deprotonated molecular ions [M–H]−, which underwent two major fragment pathways of the allyl scission and the β-fission of the alcoholic hydroxyl group. By comparison of their molecular ions and abundant fragment ions with those of reference compounds, they were tentatively assigned as 15,16-dihydroxy-9Z,12Z-octadecadienoic acid (1), 10,11,12-trihydroxy-(7Z,14Z)-heptadecadienoic acid (2), 7,15,16-trihydroxy-9Z,12Z-octadecadienoic acid (3), 15,16-dihydroxy-9Z,12Z-octadecadienoic acid (4), 15-hydroxy-6Z,9Z,12Z-octadecatrienoic acid (5), 15-hydroxy-9Z,12Z- octadecadienoic acid (6), and 15-hydroxy-12Z-octadecaenoic acid (7), respectively. Compounds 3, 5, and 7 are reported for the first time.

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Bourboula, Asimina, Dimitris Limnios, Maroula G. Kokotou, Olga G. Mountanea, and George Kokotos. "Enantioselective Organocatalysis-Based Synthesis of 3-Hydroxy Fatty Acids and Fatty γ-Lactones." Molecules 24, no. 11 (May 31, 2019): 2081. http://dx.doi.org/10.3390/molecules24112081.

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3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan’s third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.

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Sjögren, Jörgen, Jesper Magnusson, Anders Broberg, Johan Schnürer, and Lennart Kenne. "Antifungal 3-Hydroxy Fatty Acids from Lactobacillus plantarum MiLAB 14." Applied and Environmental Microbiology 69, no. 12 (December 2003): 7554–57. http://dx.doi.org/10.1128/aem.69.12.7554-7557.2003.

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ABSTRACT We report the identification and chemical characterization of four antifungal substances, 3-(R)-hydroxydecanoic acid, 3-hydroxy-5-cis-dodecenoic acid, 3-(R)-hydroxydodecanoic acid and 3-(R)-hydroxytetradecanoic acid, from Lactobacillus plantarum MiLAB 14. The concentrations of the 3-hydroxy fatty acids in the supernatant followed the bacterial growth. Racemic mixtures of the saturated 3-hydroxy fatty acids showed antifungal activity against different molds and yeasts with MICs between 10 and 100 μg ml−1.

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Nawabi, Parwez, Stefan Bauer, Nikos Kyrpides, and Athanasios Lykidis. "Engineering Escherichia coli for Biodiesel Production Utilizing a Bacterial Fatty Acid Methyltransferase." Applied and Environmental Microbiology 77, no. 22 (September 16, 2011): 8052–61. http://dx.doi.org/10.1128/aem.05046-11.

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ABSTRACTThe production of low-cost biofuels in engineered microorganisms is of great interest due to the continual increase in the world's energy demands. Biodiesel is a renewable fuel that can potentially be produced in microbes cost-effectively. Fatty acid methyl esters (FAMEs) are a common component of biodiesel and can be synthesized from either triacylglycerol or free fatty acids (FFAs). Here we report the identification of a novel bacterial fatty acid methyltransferase (FAMT) that catalyzes the formation of FAMEs and 3-hydroxyl fatty acid methyl esters (3-OH-FAMEs) from the respective free acids andS-adenosylmethionine (AdoMet). FAMT exhibits a higher specificity toward 3-hydroxy free fatty acids (3-OH-FFAs) than FFAs, synthesizing 3-hydroxy fatty acid methyl esters (3-OH-FAMEs)in vivo. We have also identified bacterial members of the fatty acyl-acyl carrier protein (ACP) thioesterase (FAT) enzyme family with distinct acyl chain specificities. These bacterial FATs exhibit increased specificity toward 3-hydroxyacyl-ACP, generating 3-OH-FFAs, which can subsequently be utilized by FAMTs to produce 3-OH-FAMEs. PhaG (3-hydroxyacyl ACP:coenzyme A [CoA] transacylase) constitutes an alternative route to 3-OH-FFA synthesis; the coexpression of PhaG with FAMT led to the highest level of accumulation of 3-OH-FAMEs and FAMEs. The availability of AdoMet, the second substrate for FAMT, is an important factor regulating the amount of methyl esters produced by bacterial cells. Our results indicate that the deletion of the global methionine regulatormetJand the overexpression of methionine adenosyltransferase result in increased methyl ester synthesis.

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Sebolai, Olihile M., Carolina H. Pohl, Piet J. Botes, Catharina J. Strauss, Pieter W. J. van Wyk, Alfred Botha, and Johan L. F. Kock. "3-Hydroxy fatty acids found in capsules ofCryptococcus neoformans." Canadian Journal of Microbiology 53, no. 6 (June 2007): 809–12. http://dx.doi.org/10.1139/w07-045.

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8

Venter, Pierre, Johan L. F. Kock, Dennis J. Coetzee, Piet J. Botes, and Santosh Nigam. "The production of 3-Hydroxy fatty acids by yeast." Prostaglandins & Other Lipid Mediators 59, no. 1-6 (December 1999): 198. http://dx.doi.org/10.1016/s0090-6980(99)90433-1.

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9

Jacob, Jürgen, and Gottfried Raab. "2,3-Dihydroxy Fatty Acids-Containing Waxes in Storks (C iconiidae)." Zeitschrift für Naturforschung C 51, no. 9-10 (October 1, 1996): 743–49. http://dx.doi.org/10.1515/znc-1996-9-1021.

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Uropygial gland secretions from five out of a total of seven species forming the genus Ciconia (family Ciconiidae; order Ciconiiformes) were found to consist of mixtures of monoester waxes, diester waxes, triester waxes, and triglycerides. Monoester waxes were composed of unbranched fatty acids and alcohols, whereas diester waxes derived from both 2- and 3-hydroxy fatty acids esterified with unbranched alcohols and fatty acids. Interestingly, triester waxes were also found deriving from either 2-hydroxy alkylmalonic acids or from erythro-2,3-dihydroxy fatty acids the latter of which have not yet been found in vertebrates so far. To compare the typical mass spectrometric fragmentation of this class of compounds erythro-2,3-dihydroxyhexadecanoic acid has been synthesized

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10

Guichardant, M., and M. Lagarde. "Monohydroxylated fatty acid substrate specificity of human leukocyte 5-lipoxygenase and ω-hydroxylase." Biochemical Journal 256, no. 3 (December 15, 1988): 879–83. http://dx.doi.org/10.1042/bj2560879.

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Various monohydroxylated fatty acids were synthesized from eicosapolyenoic acids, namely arachidonic (20:4 omega-6), timnodonic (20:5 omega-3), dihomogammalinolenic (20:3 omega-6) and mead (20:3 omega-9) acids. 12-Hydroxy derivatives, as well as 12-hydroxy-5,8,10-heptadecatrienoic acid (HHT), were produced with platelets as the enzyme source, and 15-hydroxy derivatives were produced by soya bean lipoxygenase treatment. Each monohydroxylated fatty acid was incubated with human leukocytes in the presence or absence of the calcium ionophore A23187, and dihydroxylated products were analysed by h.p.l.c. 12-Hydroxy derivatives of 20:4 omega-6, 20:5 omega-3 and 20:3 omega-9 were similarly oxygenated by both the 5-lipoxygenase and the omega-hydroxylase. As expected, the 12-hydroxy derivative of 20:3 omega-6 was not a substrate for 5-lipoxygenase, but surprisingly, omega-6 oxygenated products, like 15-OH-20:4 or HHT, were not converted by the enzyme, although being potential substrates because of the presence of two double bonds at C-5 and C-8. omega-6 oxygenated derivatives were also poorly converted by leukotriene B4 omega-hydroxylase, a cytochrome P-450-dependent enzyme. It is concluded that both leukocyte 5-lipoxygenase and omega-hydroxylase exhibit a substrate specificity towards monohydroxylated fatty acids with respect to their double bonds and/or the carbon position of the alcohol function.

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11

Eggink, Gerrit, Pieter de Waard, and Gern N. M. Huijberts. "Formation of novel poly(hydroxyalkanoates) from long-chain fatty acids." Canadian Journal of Microbiology 41, no. 13 (December 15, 1995): 14–21. http://dx.doi.org/10.1139/m95-163.

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Poly(hydroxyalkanoates) (PHAs) were isolated from Pseudomonas aeruginosa 44T1 cultivated on euphorbia oil and castor oil. With the aid of 2-D proton NMR spectra and proton-detected multiple bond coherence NMR spectra the structures of the PHAs were determined. In addition to the usual PHA constituents (C6–C14 3-hydroxy fatty acids), PHAs formed from euphorbia oil contained Δ8,9-epoxy-3-hydroxy-5c-tetradecenoate, and probably Δ6,7-epoxy-3-hydroxydodecanoate and Δ4,5-epoxy-3-hydroxydecanoate. These novel constituents account for approximately 15% of the total amount of monomers and are clearly generated via β-oxidation of vernolic acid (Δ12,13-epoxy-9c-octadecenoic acid), the main component of euphorbia oil. In PHAs formed from castor oil, 7% of the monomers found were derived from ricinoleic acid (12-hydroxy-9c-octadecenoic acid). The presence of 3,8-dihydroxy-5c tetradecenoate was clearly demonstrated. Furthermore, NMR analysis strongly suggested the presence of 3,6-dihydroxydodecanoate, 6-hydroxy-3c-dodecenoate, and 4-hydroxydecanoate.Key words: poly(hydroxyalkanoates), pseudomonads, ricinoleic acid, vernolic acid.

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12

Smith, M., H. Moon, and L. Kunst. "Production of hydroxy fatty acids in the seeds of Arabidopsis thaliana." Biochemical Society Transactions 28, no. 6 (December 1, 2000): 947–50. http://dx.doi.org/10.1042/bst0280947.

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Seed-specific expression in Arabidopsis thaliana of oleate hydroxylase enzymes from castor bean and Lesquerella fendleri resulted in the accumulation of hydroxy fatty acids in the seed oil. By using various Arabidopsis mutant lines it was shown that the endoplasmic reticulum (ER) n–-3 desaturase (FAD3) and the FAE1 condensing enzyme are involved in the synthesis of polyunsaturated and very-long-chain hydroxy fatty acids, respectively. In Arabidopsis plants with an active ER Δ12-oleate desaturase the presence of hydroxy fatty acids corresponded to an increase in the levels of 18:1 and a decrease in 18:2 levels. Expression in yeast indicates that the castor hydroxylase also has a low level of desaturase activity.

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13

TSERNG, Kou-Yi, Shiow-Jen JIN, and Lin-Su CHEN. "Reduction pathway of cis-5 unsaturated fatty acids in intact rat-liver and rat-heart mitochondria: assessment with stable-isotype-labelled substrates." Biochemical Journal 313, no. 2 (January 15, 1996): 581–88. http://dx.doi.org/10.1042/bj3130581.

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Besides the conventional isomerase-mediated pathway, unsaturated fatty acids with odd-numbered double bonds are also metabolized by reduction pathways with NADPH as cofactor. The relative contributions of these pathways were measured in intact rat-liver and rat-heart mitochondria with a novel stable isotope tracer technique. A mixture of equal amounts of unlabelled cis-5-enoyl-CoA and 13C4-labelled acyl-CoA of equal chain lengths was incubated with mitochondria. The isotope distribution of 3-hydroxy fatty acids produced from the first cycle of β-oxidation was analysed with selected ion monitoring by gas chromatograph-mass spectrometer. 3-Hydroxy fatty acids produced from the reduction pathway of unsaturated fatty acids were unlabelled (m+0) whereas those produced from saturated fatty acids were labelled (m+4). The m+0 content serves to indicate the extent of reduction pathway. Rotenone treatment was used to switch the pathway completely to reduction. The extent of m+0 enrichment in untreated mitochondria normalized to the m+0 enrichment of rotenone-treated mitochondria was the percentage of reduction pathway. With this technique, cis-4-decenoate was found to be metabolized completely by the reduction pathway in both liver and heart mitochondria. cis-5-Dodecenoate was metabolized essentially by the reduction pathway in liver mitochondria, but only to 75% in heart mitochondria. When the chain length was extended to cis-5-tetradecenoate, the reduction pathway in liver mitochondria decreased to 86% and that in heart mitochondria to 65%. The effects of carnitine, clofibrate and other conditions on the reduction pathway were also studied. Enrichments of the label on saturated fatty acids and 3-hydroxy fatty acids indicated that the major pathway of reduction was not by the direct reduction of the cis-5 double bond. Instead, it is most probably by a pathway that does not involve forming a reduced saturated fatty acid first.

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Jones, P. M., A. B. Burlina, and M. J. Bennett. "Quantitative measurement of total and free 3-hydroxy fatty acids in serum or plasma samples: short-chain 3-hydroxy fatty acids are not esterified." Journal of Inherited Metabolic Disease 23, no. 7 (November 2000): 745–50. http://dx.doi.org/10.1023/a:1005643201489.

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15

Jin, S. J., C. L. Hoppel, and K. Y. Tserng. "Incomplete fatty acid oxidation. The production and epimerization of 3-hydroxy fatty acids." Journal of Biological Chemistry 267, no. 1 (January 1992): 119–25. http://dx.doi.org/10.1016/s0021-9258(18)48467-0.

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Serra, Stefano, Davide De Simeis, Antonio Castagna, and Mattia Valentino. "The Fatty-Acid Hydratase Activity of the Most Common Probiotic Microorganisms." Catalysts 10, no. 2 (January 28, 2020): 154. http://dx.doi.org/10.3390/catal10020154.

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In this work, we studied the biotechnological potential of thirteen probiotic microorganisms currently used to improve human health. We discovered that the majority of the investigated bacteria are able to catalyze the hydration reaction of the unsaturated fatty acids (UFAs). We evaluated their biocatalytic activity toward the three most common vegetable UFAs, namely oleic, linoleic, and linolenic acids. The whole-cell biotransformation experiments were performed using a fatty acid concentration of 3 g/L in anaerobic conditions. Through these means, we assessed that the main part of the investigated strains catalyzed the hydration reaction of UFAs with very high regio- and stereoselectivity. Our biotransformation reactions afforded almost exclusively 10-hydroxy fatty acid derivatives with the single exception of Lactobacillus acidophilus ATCC SD5212, which converted linoleic acid in a mixture of 13-hydroxy and 10-hydroxy derivatives. Oleic, linoleic, and linolenic acids were transformed into (R)-10-hydroxystearic acid, (S)-(12Z)-10-hydroxy-octadecenoic, and (S)-(12Z,15Z)-10-hydroxy-octadecadienoic acids, respectively, usually with very high enantiomeric purity (ee > 95%). It is worth noting that the biocatalytic capabilities of the thirteen investigated strains may change considerably from each other, both in terms of activity, stereoselectivity, and transformation yields. Lactobacillus rhamnosus ATCC 53103 and Lactobacillus plantarum 299 V proved to be the most versatile, being able to efficiently and selectively hydrate all three investigated fatty acids.

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Youssef, Noha H., Kathleen E. Duncan, and Michael J. McInerney. "Importance of 3-Hydroxy Fatty Acid Composition of Lipopeptides for Biosurfactant Activity." Applied and Environmental Microbiology 71, no. 12 (December 2005): 7690–95. http://dx.doi.org/10.1128/aem.71.12.7690-7695.2005.

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ABSTRACT Biosurfactant production may be an economic approach to improving oil recovery. To obtain candidates most suitable for oil recovery, 207 strains, mostly belonging to the genus Bacillus, were tested for growth and biosurfactant production in medium with 5% NaCl under aerobic and anaerobic conditions. All strains grew aerobically with 5% NaCl, and 147 strains produced a biosurfactant. Thirty-five strains grew anaerobically with 5% NaCl, and two produced a biosurfactant. In order to relate structural differences to activity, eight lipopeptide biosurfactants with different specific activities produced by various Bacillus species were purified by a new protocol. The amino acid compositions of the eight lipopeptides were the same (Glu/Gln:Asp/Asn:Val:Leu, 1:1:1:4), but the fatty acid compositions differed. Multiple regression analysis showed that the specific biosurfactant activity depended on the ratios of both iso to normal even-numbered fatty acids and anteiso to iso odd-numbered fatty acids. A multiple regression model accurately predicted the specific biosurfactant activities of four newly purified biosurfactants (r 2 = 0.91). The fatty acid composition of the biosurfactant produced by Bacillus subtilis subsp. subtilis strain T89-42 was altered by the addition of branched-chain amino acids to the growth medium. The specific activities of biosurfactants produced in cultures with different amino acid additions were accurately predicted by the multiple regression model derived from the fatty acid compositions (r 2 = 0.95). Our work shows that many strains of Bacillus mojavensis and Bacillus subtilis produce biosurfactants and that the fatty acid composition is important for biosurfactant activity.

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Costa, Catarina G., Lambertus Dorland, Ulbe Holwerda, Isabel Tavares de Almeida, Bwee-Tien Poll-The, Cornelis Jakobs, and Marinus Duran. "Simultaneous analysis of plasma free fatty acids and their 3-hydroxy analogs in fatty acid β-oxidation disorders." Clinical Chemistry 44, no. 3 (March 1, 1998): 463–71. http://dx.doi.org/10.1093/clinchem/44.3.463.

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Abstract We present a new derivatization procedure for the simultaneous gas chromatographic–mass spectrometric analysis of free fatty acids and 3-hydroxyfatty acids in plasma. Derivatization of target compounds involved trifluoroacetylation of hydroxyl groups and tert-butyldimethylsilylation of the carboxyl groups. This new derivatization procedure had the advantage of allowing the complete baseline separation of free fatty acids and 3-hydroxyfatty acids while the superior gas chromatographic and mass spectrometric properties of tert-butyldimethylsilyl derivatives remained unchanged, permitting a sensitive analysis of the target compounds. Thirty-nine plasma samples from control subjects and patients with known defects of mitochondrial fatty acid β-oxidation were analyzed. A characteristic increase of long-chain 3-hydroxyfatty acids was observed for all of the long-chain 3-hydroxyacyl-CoA dehydrogenase-deficient and mitochondrial trifunctional protein-deficient plasma samples. For medium-chain acyl-CoA dehydrogenase deficiency and very-long-chain acyl-CoA dehydrogenase deficiency, decenoic and tetradecenoic acids, respectively, were the main abnormal fatty acids, whereas the multiple acyl-CoA dehydrogenase-deficient patients showed variable increases of these unusual intermediates. The results showed that this selective and sensitive method is a powerful tool in the diagnosis and monitoring of mitochondrial fatty acid β-oxidation disorders.

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Black, Brenna A., Emanuele Zannini, Jonathan M. Curtis, and Michael G. Gänzle. "Antifungal Hydroxy Fatty Acids Produced during Sourdough Fermentation: Microbial and Enzymatic Pathways, and Antifungal Activity in Bread." Applied and Environmental Microbiology 79, no. 6 (January 11, 2013): 1866–73. http://dx.doi.org/10.1128/aem.03784-12.

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ABSTRACTLactobacilli convert linoleic acid to hydroxy fatty acids; however, this conversion has not been demonstrated in food fermentations and it remains unknown whether hydroxy fatty acids produced by lactobacilli have antifungal activity. This study aimed to determine whether lactobacilli convert linoleic acid to metabolites with antifungal activity and to assess whether this conversion can be employed to delay fungal growth on bread. Aqueous and organic extracts from seven strains of lactobacilli grown in modified De Man Rogosa Sharpe medium or sourdough were assayed for antifungal activity.Lactobacillus hammesiiexhibited increased antifungal activity upon the addition of linoleic acid as a substrate. Bioassay-guided fractionation attributed the antifungal activity ofL. hammesiito a monohydroxy C18:1fatty acid. Comparison of its antifungal activity to those of other hydroxy fatty acids revealed that the monohydroxy fraction fromL. hammesiiand coriolic (13-hydroxy-9,11-octadecadienoic) acid were the most active, with MICs of 0.1 to 0.7 g liter−1. Ricinoleic (12-hydroxy-9-octadecenoic) acid was active at a MIC of 2.4 g liter−1.L. hammesiiaccumulated the monohydroxy C18:1fatty acid in sourdough to a concentration of 0.73 ± 0.03 g liter−1(mean ± standard deviation). Generation of hydroxy fatty acids in sourdough also occurred through enzymatic oxidation of linoleic acid to coriolic acid. The use of 20% sourdough fermented withL. hammesiior the use of 0.15% coriolic acid in bread making increased the mold-free shelf life by 2 to 3 days or from 2 to more than 6 days, respectively. In conclusion,L. hammesiiconverts linoleic acid in sourdough and the resulting monohydroxy octadecenoic acid exerts antifungal activity in bread.

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Sebastian, Aleksandra, and Lennart Larsson. "Characterization of the Microbial Community in Indoor Environments: a Chemical-Analytical Approach." Applied and Environmental Microbiology 69, no. 6 (June 2003): 3103–9. http://dx.doi.org/10.1128/aem.69.6.3103-3109.2003.

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ABSTRACT An integrated procedure is presented whereby gas chromatography-ion trap mass spectrometry is used to determine chemical markers of gram-negative bacterial lipopolysaccharide (3-hydroxy fatty acids with 10 to 18 carbon atoms), gram-positive bacteria (branched-chain fatty acids with 15 and 17 carbon atoms), bacterial peptidoglycan (muramic acid), and fungal biomass (ergosterol) in samples of settled house dust. A hydrolysate of 13C-labeled cyanobacterial cells is used as an internal standard for the first three markers. These analyses require two dust samples, one for 3-OH fatty acids, branched-chain fatty acids, and muramic acid and another for ergosterol. The method may be used to characterize microbial communities in environmental samples.

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Sahoo, Prakash Kumar, and Sathish Kumar Natarajan. "3‐hydroxy fatty acids Induce Placental Trophoblast Necroptosis during Acute Fatty Liver of Pregnancy." FASEB Journal 34, S1 (April 2020): 1. http://dx.doi.org/10.1096/fasebj.2020.34.s1.02385.

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Nikolova, Nelly, Tomas Rezanka, and Boryana Nikolova-Damyanova. "Fatty Acid Profiles of Main Lipid Classes in Adult Chrysomela vigintipunctata (Scopoli) (Coleopterai:Chrysomelidae)." Zeitschrift für Naturforschung C 55, no. 7-8 (August 1, 2000): 661–66. http://dx.doi.org/10.1515/znc-2000-7-828.

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Abstract The fatty acid composition of the willow leaf beetle Chrysomela vigintipunctata (Scopoli) (Coleoptera: Chrysomelidae) is presented in this paper. Fatty acids in the total lipid extract, triacylglycerols, free fatty acids and polar lipids were compared. One hundred and fifteen fatty acids were identified in the total lipids. The mixture comprised compounds with normal and branched-chains of 12-30 carbon atoms and zero to six double bonds in different positions in the carbon chain. Substantial amounts of unsaturated eicosanoic fatty acids known as important precursor of eicosanoids in insects were detected in the lipids as were biologically significant positionally isomeric dienes, trienes and tetraenes of the series (n-3) and (n-6) of C16, C18, and C22 fatty acids. Also present was a mixture of hydroxy-FA. Triacylglycerols contained mostly saturated and monounsaturated fatty acids. Polyunsaturated fatty acids were found mostly in free fatty acids and especially in polar lipids.

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Ciccoli, Roberto, Shakti Sahi, Sandhya Singh, Hridayesh Prakash, Maria-Patapia Zafiriou, Ganchimeg Ishdorj, Johan L. F. Kock, and Santosh Nigam. "Oxygenation by COX-2 (cyclo-oxygenase-2) of 3-HETE (3-hydroxyeicosatetraenoic acid), a fungal mimetic of arachidonic acid, produces a cascade of novel bioactive 3-hydroxyeicosanoids." Biochemical Journal 390, no. 3 (September 5, 2005): 737–47. http://dx.doi.org/10.1042/bj20041995.

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Cyclo-oxygenases-1/2 (COX-1/2) catalyse the oxygenation of AA (arachidonic acid) and related polyunsaturated fatty acids to endoperoxide precursors of prostanoids. COX-1 is referred to as a constitutive enzyme involved in haemostasis, whereas COX-2 is an inducible enzyme expressed in inflammatory diseases and cancer. The fungus Dipodascopsis uninucleata has been shown by us to convert exogenous AA into 3(R)-HETE [3(R)-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid]. 3R-HETE is stereochemically identical with AA, except that a hydroxy group is attached at its C-3 position. Molecular modelling studies with 3-HETE and COX-1/2 revealed a similar enzyme–substrate structure as reported for AA and COX-1/2. Here, we report that 3-HETE is an appropriate substrate for COX-1 and -2, albeit with a lower activity of oxygenation than AA. Oxygenation of 3-HETE by COX-2 produced a novel cascade of 3-hydroxyeicosanoids, as identified with EI (electron impact)–GC–MS, LC–MS–ES (electrospray) and LC–MS–API (atmospheric pressure ionization) methods. Evidence for in vitro production of 3-hydroxy-PGE2 (3-hydroxy-prostaglandin E2) was obtained upon infection of HeLa cells with Candida albicans at an MOI (multiplicity of infection) of 100. Analogous to interaction of AA and aspirin-treated COX-2, 3-HETE was transformed by acetylated COX-2 to 3,15-di-HETE (3,15-dihydroxy-HETE), whereby C-15 showed the (R)-stereochemistry. 3-Hydroxy-PGs are potent biologically active compounds. Thus 3-hydroxy-PGE2 induced interleukin-6 gene expression via the EP3 receptor (PGE2 receptor 3) in A549 cells, and raised cAMP levels via the EP4 receptor in Jurkat cells. Moreover, 3R,15S-di-HETE triggered the opening of the K+ channel in HTM (human trabecular meshwork) cells, as measured by the patch–clamp technique. Since many fatty acid disorders are associated with an ‘escape’ of 3-hydroxy fatty acids from the β-oxidation cycle, the production of 3-hydroxyeicosanoids may be critical in modulation of effects of endogenously produced eicosanoids.

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Xi, Yinwei, Liuyan Wang, Yasong Wang, Huangmin Ge, Mingxing Zhang, Shengjie Ye, Xueqin Zhao, and Yunping Xu. "Distribution of 3-hydroxy fatty acids in South China Sea since the last deglaciation: Applicability of 3-hydroxy fatty acid-based palaeothermometry." Chemical Geology 652 (May 2024): 122024. http://dx.doi.org/10.1016/j.chemgeo.2024.122024.

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Butt, Yasmeen M., Samira A. Kamrudin, and Dinesh Rakheja. "Highly Active Antiretroviral Therapy Does Not Affect Mitochondrial β-Oxidation of Fatty Acids: An in Vitro Study in Fibroblasts." Pediatric and Developmental Pathology 11, no. 1 (January 2008): 35–38. http://dx.doi.org/10.2350/06-11-0186.1.

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Preeclampsia is a multifactorial pregnancy-specific disease. In some cases, severe preeclampsia and related disorders of acute fatty liver of pregnancy and hemolysis, elevated liver enzymes, low platelets syndrome are associated with inherited defects in mitochondrial β-oxidation of fatty acids, especially a deficiency of long-chain 3-hydroxyacyl coenzyme A dehydrogenase (LCHAD). Recently, an unexplained increase in the incidence of preeclampsia has been documented in human immunodeficiency virus (HIV)–infected pregnant women on treatment with highly active antiretroviral therapy (HAART). We performed this study to determine if antiretroviral drugs affect mitochondrial β-oxidation fatty acids in vitro. Two normal and 1 heterozygous LCHAD-deficient cell lines were exposed to up to 5 times the therapeutic concentrations of the following antiretroviral drugs: nevirapine, didanosine, lamivudine, and a combination of nelfinavir, zidovudine, and lamivudine. One homozygous LCHAD-deficient cell line served as the positive control. After exposure of the fibroblasts to these drugs for periods ranging from 2 to 10 days, accumulations of even-chain 3-hydroxy fatty acids (3-OH-C6 to 3-OH-C18) in the culture media were measured by stable-isotope dilution gas chromatography/mass spectrometry. Compared to the respective unexposed fibroblasts, there was no significant build-up of 3-hydroxy fatty acids in the culture media of normal or heterozygous LCHAD-deficient fibroblasts exposed to antiretroviral drugs. Our results show that the commonly used antiretroviral drugs do not adversely affect fatty acid oxidation in fibroblasts. Therefore, an altered fatty acid oxidation may not be the mechanism for the reported increased risk of preeclampsia in HIV-infected pregnant women on HAART.

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Racovita, Radu C., Chen Peng, Takayoshi Awakawa, Ikuro Abe, and Reinhard Jetter. "Very-long-chain 3-hydroxy fatty acids, 3-hydroxy fatty acid methyl esters and 2-alkanols from cuticular waxes of Aloe arborescens leaves." Phytochemistry 113 (May 2015): 183–94. http://dx.doi.org/10.1016/j.phytochem.2014.08.005.

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Jenske, Ramona, and Walter Vetter. "Enantioselective Analysis of 2- and 3-Hydroxy Fatty Acids in Food Samples." Journal of Agricultural and Food Chemistry 56, no. 24 (December 24, 2008): 11578–83. http://dx.doi.org/10.1021/jf802772a.

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Ferrando, Raúl, Bogumila Szponar, Arturo Sánchez, Lennart Larsson, and Pedro L. Valero-Guillén. "3-Hydroxy fatty acids in saliva as diagnostic markers in chronic periodontitis." Journal of Microbiological Methods 62, no. 3 (September 2005): 285–91. http://dx.doi.org/10.1016/j.mimet.2005.04.014.

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Jenske, Ramona, and Walter Vetter. "Concentrations of medium-chain 2- and 3-hydroxy fatty acids in foodstuffs." Food Chemistry 114, no. 3 (June 2009): 1122–29. http://dx.doi.org/10.1016/j.foodchem.2008.10.067.

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Balzano, Sergio, Laura Villanueva, Marijke de Bar, Diana X. Sahonero Canavesi, Caglar Yildiz, Julia C. Engelmann, Eric Marechal, Josselin Lupette, Jaap S. Sinninghe Damstï¿½, and Stefan Schouten. "Biosynthesis of Long Chain Alkyl Diols and Long Chain Alkenols in Nannochloropsis spp. (Eustigmatophyceae)." Plant and Cell Physiology 60, no. 8 (May 6, 2019): 1666–82. http://dx.doi.org/10.1093/pcp/pcz078.

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AbstractWe investigated potential biosynthetic pathways of long chain alkenols (LCAs), long chain alkyl diols (LCDs), and long chain hydroxy fatty acids (LCHFAs) in Nannochloropsis oceanica and Nannochloropsis gaditana, by combining culturing experiments with genomic and transcriptomic analyses. Incubation of Nannochloropsis spp. in the dark for 1 week led to significant increases in the cellular concentrations of LCAs and LCDs in both species. Consistently, 13C-labelled substrate experiments confirmed that both LCA and LCD were actively produced in the dark from C14–18 fatty acids by either condensation or elongation/hydroxylation, although no enzymatic evidence was found for the former pathway. Nannochloropsis spp. did, however, contain (i) multiple polyketide synthases (PKSs) including one type (PKS-Clade II) that might catalyze incomplete fatty acid elongations leading to the formation of 3-OH-fatty acids, (ii) 3-hydroxyacyl dehydratases (HADs), which can possibly form Δ2/Δ3 monounsaturated fatty acids, and (iii) fatty acid elongases (FAEs) that could elongate 3-OH-fatty acids and Δ2/Δ3 monounsaturated fatty acids to longer products. The enzymes responsible for reduction of the long chain fatty acids to LCDs and LCAs are, however, unclear. A putative wax ester synthase/acyl coenzyme A (acyl-CoA): diacylglycerol acyltransferase is likely to be involved in the esterification of LCAs and LCDs in the cell wall. Our data thus provide useful insights in predicting the biosynthetic pathways of LCAs and LCDs in phytoplankton suggesting a key role of FAE and PKS enzymes.

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Keinänen, Minna M., Leena K. Korhonen, Markku J. Lehtola, Ilkka T. Miettinen, Pertti J. Martikainen, Terttu Vartiainen, and Merja H. Suutari. "The Microbial Community Structure of Drinking Water Biofilms Can Be Affected by Phosphorus Availability." Applied and Environmental Microbiology 68, no. 1 (January 2002): 434–39. http://dx.doi.org/10.1128/aem.68.1.434-439.2002.

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ABSTRACT Microbial communities in biofilms grown for 4 and 11 weeks under the flow of drinking water supplemented with 0, 1, 2, and 5 μg of phosphorus liter−1 and in drinking and warm waters were compared by using phospholipid fatty acids (PLFAs) and lipopolysaccharide 3-hydroxy fatty acids (LPS 3-OH-FAs). Phosphate increased the proportion of PLFAs 16:1ω7c and 18:1ω7c and affected LPS 3-OH-FAs after 11 weeks of growth, indicating an increase in gram-negative bacteria and changes in their community structure. Differences in community structures between biofilms and drinking and warm waters can be assumed from PLFAs and LPS 3-OH-FAs, concomitantly with adaptive changes in fatty acid chain length, cyclization, and unsaturation.

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Guichardant, M., B. Chantegrel, C. Deshayes, A. Doutheau, P. Moliere, and M. Lagarde. "Specific markers of lipid peroxidation issued from n−3 and n−6 fatty acids." Biochemical Society Transactions 32, no. 1 (February 1, 2004): 139–40. http://dx.doi.org/10.1042/bst0320139.

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Several markers of lipid peroxidation are available with different degrees of specificity, from malondialdehyde as a global marker, to F2-isoprostane, which is specifically produced from arachidonic acid. Among these, 4-hydroxynonenal is recognized as a breakdown product of fatty acid hydroperoxides, such as 15-hydroperoxy-eicosatetraenoic acid and 13-hydroperoxy-octade cadienoic acid from the n−6 fatty acids. Furthermore, 4-hydroxyhexenal (4-HHE) derives from n−3 fatty acid hydroperoxides. We have recently described the occurrence of 4-hydroxydodecadienal (4-HDDE) from the 12-lipoxygenase product of arachidonic acid 12-hydroperoxy-eicosatetraenoic acid. These three hydroxy-alkenals may be measured in human plasma by GC–MS, but they may partly be generated in the course of sampling, and the relative volatility of 4-HHE makes its measurement quite unreliable. We have successfully characterized and measured the stable oxidized carboxylic acid products from the hydroxy-alkenals 4-HNA, 4-HHA and 4-HDDA in urine. The ratio between 4-HHA and 4-HNA found in the same urinary sample might provide useful information on the location of lipid peroxidation, accounting for the high enrichment of the cerebrovascular system with docosahexaenoic acid, the main n−3 fatty acid in humans.

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Mountanea, Olga G., Christiana Mantzourani, Dimitrios Gkikas, Panagiotis K. Politis, and George Kokotos. "Asymmetric Synthesis of Saturated and Unsaturated Hydroxy Fatty Acids (HFAs) and Study of Their Antiproliferative Activity." Biomolecules 14, no. 1 (January 15, 2024): 110. http://dx.doi.org/10.3390/biom14010110.

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Hydroxy fatty acids (HFAs) constitute a class of lipids, distinguished by the presence of a hydroxyl on a long aliphatic chain. This study aims to expand our insights into HFA bioactivities, while also introducing new methods for asymmetrically synthesizing unsaturated and saturated HFAs. Simultaneously, a procedure previously established by us was adapted to generate new HFA regioisomers. An organocatalytic step was employed for the synthesis of chiral terminal epoxides, which either by alkynylation or by Grignard reagents resulted in unsaturated or saturated chiral secondary alcohols and, ultimately, HFAs. 7-(S)-Hydroxyoleic acid (7SHOA), 7-(S)-hydroxypalmitoleic acid (7SHPOA) and 7-(R)- and (S)-hydroxymargaric acids (7HMAs) were synthesized for the first time and, together with regioisomers of (R)- and (S)-hydroxypalmitic acids (HPAs) and hydroxystearic acids (HSAs), whose biological activity has not been tested so far, were studied for their antiproliferative activities. The unsaturation of the long chain, as well as an odd-numbered (C17) fatty acid chain, led to reduced activity, while the new 6-(S)-HPA regioisomer was identified as exhibiting potent antiproliferative activity in A549 cells. 6SHPA induced acetylation of histone 3 in A549 cells, without affecting acetylated α-tubulin levels, suggesting the selective inhibition of histone deacetylase (HDAC) class I enzymes, and was found to inhibit signal transducer and activator of transcription 3 (STAT3) expression.

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DIEUAIDE-NOUBHANI, Martine, Stanny ASSELBERGHS, Guy P. MANNAERTS, and Paul P. VAN VELDHOVEN. "Evidence that multifunctional protein 2, and not multifunctional protein 1, is involved in the peroxisomal β-oxidation of pristanic acid." Biochemical Journal 325, no. 2 (July 15, 1997): 367–73. http://dx.doi.org/10.1042/bj3250367.

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The second (enoyl-CoA hydratase) and third (3-hydroxyacyl-CoA dehydrogenase) steps of peroxisomal β-oxidation are catalysed by two separate multifunctional proteins (MFPs), MFP-1 being involved in the degradation of straight-chain fatty acids and MFP-2 in the β-oxidation of the side chain of cholesterol (bile acid synthesis). In the present study we determined which of the two MFPs is involved in the peroxisomal degradation of pristanic acid by using the synthetic analogue 2-methylpalmitic acid. The four stereoisomers of 3-hydroxy-2-methylpalmitoyl-CoA were separated by gas chromatography after hydrolysis, methylation and derivatization of the hydroxy group with (S)-2-phenylpropionic acid, and the stereoisomers were designated I–IV according to their order of elution from the column. Purified MFP-1 dehydrated stereoisomer IV but dehydrogenated stereoisomer III, so by itself MFP-1 is not capable of converting a branched enoyl-CoA into a 3-ketoacyl-CoA. In contrast, MFP-2 dehydrated and dehydrogenated the same stereoisomer (II), so it is highly probable that MFP-2 is involved in the peroxisomal degradation of branched fatty acids and that stereoisomer II is the physiological intermediate in branched fatty acid oxidation. By analogy with the results obtained with the four stereoisomers of the bile acid intermediate varanoyl-CoA, stereoisomer II can be assigned the 3R-hydroxy, 2R-methyl configuration.

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Dajnowska, Aleksandra, Ewa Tomaszewska, Sylwester Świątkiewicz, Anna Arczewska-Włosek, Piotr Dobrowolski, Piotr Domaradzki, Halyna Rudyk, et al. "Yolk Fatty Acid Profile and Amino Acid Composition in Eggs from Hens Supplemented with ß-Hydroxy-ß-Methylbutyrate." Foods 12, no. 20 (October 11, 2023): 3733. http://dx.doi.org/10.3390/foods12203733.

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In recent years, a supplementation of livestock animals, including poultry, with β-Hydroxy-β-methylbutyrate (HMB) has gained attention for its effects on protein and fat metabolism. This study investigates the effects of HMB in the laying hen diet on egg quality, focusing on amino acid and fatty acid composition. Laying hens were supplemented with 0.02% HMB, with performance parameters and egg components analyzed. HMB supplementation led to increased albumen weight, influencing egg weight while also reducing feed intake per egg without affecting laying rate, yolk indices, fat, or cholesterol content. Notably, the study revealed significant changes in egg amino acid and fatty acid profiles due to HMB supplementation. Various amino acids, including glycine, serine, and isoleucine, were altered in the yolk, impacting nutritional value and potential health benefits. Regarding fatty acids, the study observed changes in both saturated as well as n-6 and n-3 fatty acids, affecting the overall lipid profile of egg yolks. However, the shifts in fatty acid composition could have implications for cardiovascular health due to altered ratios of n-6/n-3 fatty acids. Further research is required to comprehensively understand the implications of these findings for consumer-oriented egg quality and health benefits.

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Santalova, Elena A., and Vasily I. Svetashev. "Preparation of 4,4-Dimethyloxazoline and Pyrrolidine Derivatives from Fatty Acid Methyl Esters Using Sodium Borohydride: Mild and Simple One-Pot Derivatization Procedures for a Gas Chromatographic–Mass Spectrometric Analysis of Fatty Acids." Natural Product Communications 17, no. 10 (October 2022): 1934578X2211314. http://dx.doi.org/10.1177/1934578x221131408.

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Procedures for preparing 4,4-dimethyloxazoline (DMOX) and pyrrolidine derivatives from fatty acid methyl esters (FAMEs) were modified to provide milder and simpler conditions for the derivatization reactions widely used in the mass spectrometric analysis of fatty acids. DMOX and pyrrolidine derivatives were obtained overnight at room temperature in the presence of sodium borohydride. The proposed method, involving a low-temperature condensation-cyclization of FAME to DMOX, allows for the direct preparation of DMOX derivatives from non-hydroxy, 2- and 3-hydroxy acid methyl esters. The described simple one-pot procedures are “mild” alternatives to existing methods, which require the use of elevated temperatures.

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Kawahara, Kazuyoshi. "Variation, Modification and Engineering of Lipid A in Endotoxin of Gram-Negative Bacteria." International Journal of Molecular Sciences 22, no. 5 (February 25, 2021): 2281. http://dx.doi.org/10.3390/ijms22052281.

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Lipid A of Gram-negative bacteria is known to represent a central role for the immunological activity of endotoxin. Chemical structure and biosynthetic pathways as well as specific receptors on phagocytic cells had been clarified by the beginning of the 21st century. Although the lipid A of enterobacteria including Escherichia coli share a common structure, other Gram-negative bacteria belonging to various classes of the phylum Proteobacteria and other taxonomical groups show wide variety of lipid A structure with relatively decreased endotoxic activity compared to that of E. coli. The structural diversity is produced from the difference of chain length of 3-hydroxy fatty acids and non-hydroxy fatty acids linked to their hydroxyl groups. In some bacteria, glucosamine in the backbone is substituted by another amino sugar, or phosphate groups bound to the backbone are modified. The variation of structure is also introduced by the enzymes that can modify electrostatic charges or acylation profiles of lipid A during or after its synthesis. Furthermore, lipid A structure can be artificially modified or engineered by the disruption and introduction of biosynthetic genes especially those of acyltransferases. These technologies may produce novel vaccine adjuvants or antagonistic drugs derived from endotoxin in the future.

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Nakagawa, Yoji, and Tohey Matsuyama. "Chromatographic determination of optical configuration of 3-hydroxy fatty acids composing microbial surfactants." FEMS Microbiology Letters 108, no. 1 (March 1993): 99–102. http://dx.doi.org/10.1111/j.1574-6968.1993.tb06080.x.

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Yang, Yi, Canfa Wang, James A. Bendle, Xiaoguo Yu, Chao Gao, Xiaoxia Lü, Xiaoyan Ruan, Ruicheng Wang, and Shucheng Xie. "A new sea surface temperature proxy based on bacterial 3-hydroxy fatty acids." Organic Geochemistry 141 (March 2020): 103975. http://dx.doi.org/10.1016/j.orggeochem.2020.103975.

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40

Szponar, Bogumiła, Leonard Kraśnik, Tomasz Hryniewiecki, Andrzej Gamian, and Lennart Larsson. "Distribution of 3-Hydroxy Fatty Acids in Tissues after Intraperitoneal Injection of Endotoxin." Clinical Chemistry 49, no. 7 (July 1, 2003): 1149–53. http://dx.doi.org/10.1373/49.7.1149.

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Abstract Background: 3-Hydroxy fatty acids (3-OH FAs) with 10- to 18-carbon chain lengths are constituents of the endotoxin [lipopolysaccharide (LPS)] of gram-negative bacteria. We investigated whether these FAs may be used as chemical markers in measuring endotoxin concentrations in mammalian tissue samples. Methods: We used gas-liquid chromatography–tandem mass spectrometry to measure 3-OH FAs in serum and tissues (heart, liver, and skeletal muscles) of rats after intraperitoneal injection of Escherichia coli LPS. One group of rats (group I) received a single LPS dose of 20 mg/kg of body weight; group II rats received the same total dose but over the course of 10 days (2 mg/kg each day). Rats receiving saline (group III) were used as controls. Results: 3-OH FAs with chain lengths of 10, 12, 14, 16, and 18 carbons were detected in all studied types of samples. Group I rats had 50-fold and group II rats had 3-fold higher serum concentrations of 3-hydoxytetradecanoic acid (3-OH 14:0, the predominant 3-OH FA of E. coli LPS) than group III rats. Concentrations of 3-OH 14:0 in livers from group I and II rats were similar and fourfold higher than in group III rats, whereas concentrations of the same acid in skeletal and heart tissues did not differ among the three groups of rats. 3-OH 14:0 dominated in heart and liver of group III rats, whereas 3-OH 16:0 (followed by 3-OH 14:0) dominated in skeletal muscles and blood. Conclusions: 3-OH FAs 10–18 carbons in length, probably originating from endotoxin and mitochondrial β-oxidation, are abundant in rat liver, skeletal muscles, and heart and can also be detected in blood. The widespread presence of these compounds in mammals limits their usefulness as LPS markers for endotoxin in clinical samples.

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Schneider, Silke, Marcel G. Wubbolts, Dominique Sanglard, and Bernard Witholt. "Biocatalyst Engineering by Assembly of Fatty Acid Transport and Oxidation Activities for In Vivo Application of Cytochrome P-450BM-3 Monooxygenase." Applied and Environmental Microbiology 64, no. 10 (October 1, 1998): 3784–90. http://dx.doi.org/10.1128/aem.64.10.3784-3790.1998.

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ABSTRACT The application of whole cells containing cytochrome P-450BM-3 monooxygenase [EC 1.14.14.1 ] for the bioconversion of long-chain saturated fatty acids to ω-1, ω-2, and ω-3 hydroxy fatty acids was investigated. We utilized pentadecanoic acid and studied its conversion to a mixture of 12-, 13-, and 14-hydroxypentadecanoic acids by this monooxygenase. For this purpose,Escherichia coli recombinants containing plasmid pCYP102 producing the fatty acid monooxygenase cytochrome P-450BM-3were used. To overcome inefficient uptake of pentadecanoic acid by intact E. coli cells, we made use of a cloned fatty acid uptake system from Pseudomonas oleovorans which, in contrast to the common FadL fatty acid uptake system of E. coli, does not require coupling by FadD (acyl-coenzyme A synthetase) of the imported fatty acid to coenzyme A. This system fromP. oleovorans is encoded by a gene carried by plasmid pGEc47, which has been shown to effect facilitated uptake of oleic acid in E. coli W3110 (M. Nieboer, Ph.D. thesis, University of Groningen, Groningen, The Netherlands, 1996). By using a double recombinant of E. coli K27, which is a fadDmutant and therefore unable to consume substrates or products via the β-oxidation cycle, a twofold increase in productivity was achieved. Applying cytochrome P-450BM-3 monooxygenase as a biocatalyst in whole cells does not require the exogenous addition of the costly cofactor NADPH. In combination with the coenzyme A-independent fatty acid uptake system from P. oleovorans, cytochrome P-450BM-3 recombinants appear to be useful alternatives to the enzymatic approach for the bioconversion of long-chain fatty acids to subterminal hydroxylated fatty acids.

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Aarti, Sati, and Bhatt Priyanka. "REVIEW ON THERAPEUTIC EFFECTS MEDIATED BY OMEGA-3 FATTY ACIDS IN ALZHEIMER’S DISEASE." Asian Journal of Pharmaceutical and Clinical Research 11, no. 2 (February 1, 2018): 54. http://dx.doi.org/10.22159/ajpcr.2018.v11i2.22435.

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Alzheimer’s disease (AD) is a neurodegenerative disorder with relevant unmet therapeutic needs. Both natural aging and AD have been associated with a significant decline in the Omega-3 polyunsaturated fatty acid, docosahexaenoic acid (DHA), and accordingly, administration of DHA has been proposed as a possible treatment for this pathology. DHA and its derivatives like 2-hydroxy DHA-(OHDHA) have a strong therapeutic potential to treat AD. Studies have demonstrated that DHA induced lipid modifications are paralleled with a reduction in amyloid-beta (Αβ) accumulation and full recovery of cognitive impairment. Omega-3 fatty acids also caused alterations in the subcellular distribution of secretases and reduced Αβ-induced tau protein phosphorylation as well. Furthermore, OHDHA enhanced the survival of neuron-like differentiated cells exposed to different insults such as oligomeric Αβ and N-methyl-D-aspartate-mediated neurotoxicity. In conclusion, this review focuses on the pleiotropic effects of Omega-3 fatty acids that might prove beneficial to treat AD.

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Seong, Su Hui, Duc Hung Nguyen, Aditi Wagle, Mi Hee Woo, Hyun Ah Jung, and Jae Sue Choi. "Experimental and Computational Study to Reveal the Potential of Non-Polar Constituents from Hizikia fusiformis as Dual Protein Tyrosine Phosphatase 1B and α-Glucosidase Inhibitors." Marine Drugs 17, no. 5 (May 22, 2019): 302. http://dx.doi.org/10.3390/md17050302.

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Hizikia fusiformis (Harvey) Okamura is an edible marine alga that has been widely used in Korea, China, and Japan as a rich source of dietary fiber and essential minerals. In our previous study, we observed that the methanol extract of H. fusiformis and its non-polar fractions showed potent protein tyrosine phosphatase 1B (PTP1B) and α-glucosidase inhibition. Therefore, the aim of the present study was to identify the active ingredient in the methanol extract of H. fusiformis. We isolated a new glycerol fatty acid (13) and 20 known compounds including 9 fatty acids (1–3, 7–12), mixture of 24R and 24S-saringosterol (4), fucosterol (5), mixture of 24R,28R and 24S,28R-epoxy-24-ethylcholesterol (6), cedrusin (14), 1-(4-hydroxy-3-methoxyphenyl)-2-[2-hydroxy -4-(3-hydroxypropyl)phenoxy]-1,3-propanediol (15), benzyl alcohol alloside (16), madhusic acid A (17), glycyrrhizin (18), glycyrrhizin-6’-methyl ester (19), apo-9′-fucoxanthinone (20) and tyramine (21) from the non-polar fraction of H. fusiformis. New glycerol fatty acid 13 was identified as 2-(7′- (2″-hydroxy-3″-((5Z,8Z,11Z)-icosatrienoyloxy)propoxy)-7′-oxoheptanoyl)oxymethylpropenoic acid by spectroscopic analysis using NMR, IR, and HR-ESI-MS. We investigated the effect of the 21 isolated compounds and metabolites (22 and 23) of 18 against the inhibition of PTP1B and α-glucosidase enzymes. All fatty acids showed potent PTP1B inhibition at low concentrations. In particular, new compound 13 and fucosterol epoxide (6) showed noncompetitive inhibitory activity against PTP1B. Metabolites of glycyrrhizin, 22 and 23, exhibited competitive inhibition against PTP1B. These findings suggest that H. fusiformis, a widely consumed seafood, may be effective as a dietary supplement for the management of diabetes through the inhibition of PTP1B.

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Mansoorian, Bahareh, Emilie Combet, Areej Alkhaldy, Ada L. Garcia, and Christine Ann Edwards. "Impact of Fermentable Fibres on the Colonic Microbiota Metabolism of Dietary Polyphenols Rutin and Quercetin." International Journal of Environmental Research and Public Health 16, no. 2 (January 21, 2019): 292. http://dx.doi.org/10.3390/ijerph16020292.

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Dietary fibre and polyphenols are both metabolised to short-chain fatty acids (SCFAs) and phenolic acids (PA) by the colonic microbiota. These may alter microbiota growth/diversity, but their interaction is not understood. Interactions between rutin and raftiline, ispaghula or pectin were investigated in human faecal batch cultures (healthy participants; 19–33 years, 4 males, 6 females, BMI 18.4–27.4) after a low (poly)phenol diet three days prior to study. Phenolic acids were measured by gas chromatography-mass spectrometry and SCFAs by gas chromatography-flame ionisation after 2, 4, 6, and 24 h. Rutin fermentation produced Phenyl acetic acid (PAA), 4-Hydroxy benzoic acid (4-OHBA), 3-Hydroxy phenyl acetic acid (3-OHPAA), 4-Hydroxy phenyl acetic acid (4-OHPAA), 3,4-Dihydroxy phenyl acetic acid (3,4-diOHPAA), 3-Hydroxy phenyl propionic acid (3-OHPPA), and 4-Hydroxy phenyl propionic acid (4-OHPPA). 3,4-DiOHPAA and 3-OHPAA were predominant at 6 h (1.9 ± 1.8 µg/mL, 2.9 ± 2.5 µg/mL, and 0.05 ± 0.0 µg/mL, respectively) and 24 h (5.5 ± 3.3 µg/mL, 3.1 ± 4.2 µg/mL, and 1.2 ± 1.6 µg/mL). Production of all PA except 3-OHPPA and 4-OHPPA was reduced by at least one fibre. Inhibition of PA was highest for rutin (8-fold, p < 0.01), then pectin (5-fold, p < 0.01), and ispaghula (2-fold, p = 0.03). Neither rutin nor quercetin had a detectable impact on SCFA production. These interactions should be considered when assessing dietary polyphenols and potential health benefits.

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Sonesson, Anders, Erik Jantzen, Torill Tangen, and Ulrich Zähringer. "Lipopolysaccharides of Legionella erythra and Legionella oakridgensis." Canadian Journal of Microbiology 40, no. 8 (August 1, 1994): 666–71. http://dx.doi.org/10.1139/m94-105.

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The chemical composition of lipopolysaccharides from Legionella erythra and Legionella oakridgensis was analysed. Sodium dodecyl sulfate polyacrylamide gel electrophoresis showed both lipopolysaccharides to have a smooth-type character. The polysaccharide part of both lipopolysaccharides contained D-mannose, D-glucose, D-glycero-D-mannoheptose, L-glycero-D-manno-heptose, 2-keto-3-deoxyoctonic acid, L-fucosamine, D-glucosamine, and glucosamine phosphate. In addition, L-rhamnose, glycerol phosphate, and glucose phosphate were identified in the polysaccharide part of L. erythra lipopolysaccharide. The main sugar identified in the lipid A part of both lipopolysaccharides, 2,3-diamino-2,3-dideoxy-D-glucose, was found to be substituted with a complex fatty acid composition including at least 16 different amide-linked 3-hydroxy fatty acids. Both lipopolysaccharides contained nonhydroxy fatty acids and the uncommon 27-oxo-octacosanoic acid, 29-oxotriacontanoic acid, and 27-hydroxyoctacosanoic acid. The lipopolysaccharide of L. oakridgensis also contained 29-hydroxytriacontanoic acid. The dioic long-chain acids heptacosane-1,27-dioic acid and nonacosane-1,29-dioic acid were only present in the lipopolysaccharide of L. erythra.Key words: taxonomy, long-chain fatty acids, chemical analysis, 2,3-diamino-2,3-dideoxy-D-glucose.

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46

Christie, William W., and John L. Harwood. "Oxidation of polyunsaturated fatty acids to produce lipid mediators." Essays in Biochemistry 64, no. 3 (July 3, 2020): 401–21. http://dx.doi.org/10.1042/ebc20190082.

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Abstract The chemistry, biochemistry, pharmacology and molecular biology of oxylipins (defined as a family of oxygenated natural products that are formed from unsaturated fatty acids by pathways involving at least one step of dioxygen-dependent oxidation) are complex and occasionally contradictory subjects that continue to develop at an extraordinarily rapid rate. The term includes docosanoids (e.g. protectins, resolvins and maresins, or specialized pro-resolving mediators), eicosanoids and octadecanoids and plant oxylipins, which are derived from either the omega-6 (n-6) or the omega-3 (n-3) families of polyunsaturated fatty acids. For example, the term eicosanoid is used to embrace those biologically active lipid mediators that are derived from C20 fatty acids, and include prostaglandins, thromboxanes, leukotrienes, hydroxyeicosatetraenoic acids and related oxygenated derivatives. The key enzymes for the production of prostanoids are prostaglandin endoperoxide H synthases (cyclo-oxygenases), while lipoxygenases and oxidases of the cytochrome P450 family produce numerous other metabolites. In plants, the lipoxygenase pathway from C18 polyunsaturated fatty acids yields a variety of important products, especially the jasmonates, which have some comparable structural features and functions. Related oxylipins are produced by non-enzymic means (isoprostanes), while fatty acid esters of hydroxy fatty acids (FAHFA) are now being considered together with the oxylipins from a functional perspective. In all kingdoms of life, oxylipins usually act as lipid mediators through specific receptors, have short half-lives and have functions in innumerable biological contexts.

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Matsuyama, T., K. Kaneda, I. Ishizuka, T. Toida, and I. Yano. "Surface-active novel glycolipid and linked 3-hydroxy fatty acids produced by Serratia rubidaea." Journal of Bacteriology 172, no. 6 (1990): 3015–22. http://dx.doi.org/10.1128/jb.172.6.3015-3022.1990.

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48

Dahle, U. R., L. Tronstad, and I. Olsen. "3-hydroxy fatty acids in a lipopolysaccharide-like material from Treponema denticola strain FM." Dental Traumatology 12, no. 4 (August 1996): 202–5. http://dx.doi.org/10.1111/j.1600-9657.1996.tb00515.x.

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Binding, Norbert, Sabine Jaschinski, Sabine Werlich, Stefan Bletz, and Ute Witting. "Quantification of bacterial lipopolysaccharides (endotoxin) by GC–MS determination of 3-hydroxy fatty acids." J. Environ. Monit. 6, no. 1 (2004): 65–70. http://dx.doi.org/10.1039/b309237b.

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Ageyeva, Natalia, Anastasia Tikhonova, Svetlana Biryukova, and Ekaterina Globa. "Study of phenolic compounds and lipids of grape pomace." E3S Web of Conferences 285 (2021): 05018. http://dx.doi.org/10.1051/e3sconf/202128505018.

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The article is devoted to the research of the makeup of phenolic compounds and fatty acids of grape pomace. The phenolic compounds were identified in skin and seed extracts and in extracts of skin-and-seed mixtures; the fatty acids – in grape oil generated by direct pressing. It was established that anthocyanins were present mainly in the skins. Low concentrations of ten components of the anthocyanin complex were identified in the Saperavi seeds. Maximum amounts of anthocyanins were found in the Saperavi skins. The concentration of quercetin distinguished by a PP-vitamin activity was by 1.5 to 2.0 times higher in the skin-andseed mixtures, especially of Roesler grapes, than in the skin itself. Maximum amounts of flavan-3-ols, hydroxy-cinnamic and hydroxybenzoic acids and oligomeric procyanidins, as well as the highest antioxidant activity were observed in the skin-and-seed mixture. The highest value of the correlation factor was observed in cases of interaction of antioxidant activity and concentration of procyanidins (r = 0.83), antioxidant activity and concentration of anthocyanins (r = 0.78), and antioxidant activity and concentration of flavan-3-ols (r = 0.75). Among the flavan-3-ols, it was (+)-D-Catechin that prevailed in grape seeds, with its concentration in the Pinot Noir extract (OAO APF Fanagoria) reaching 468 mg/dm3. Maximum concentration of Epigallocatechin-gallate was observed in the Saperavi and Pinot Noir seeds. As regards the concentration of hydroxy-cinnamic acids in the seeds, n-coumaric acid (Ancellotta, Saperavi) stood apart among the others; gallic acid (Saperavi, Ancellotta) came forward among the hydroxy-benzoic acids. In the reviewed samples of grape seeds, procyanidins of groups В1 , В2 and В3 distinguished by high antioxidant activity prevailed. Prevalence of linoleic and oleic acids was established for grape oil extracted from the seeds of such red grape varieties as Cabernet Sauvignon, Pinot Noir and Saperavi. Maximum concentrations of oleic acid were found in the Pinot Noir and Riesling seeds. Palmitic and stearic acids were also available in rather high concentrations in the grape oil.

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Journal articles on the topic '3-hydroxy fatty acids'

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