scholarly journals Fatty Acyl Esters of Hydroxy Fatty Acid (FAHFA) Lipid Families

Metabolites ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 512
Author(s):  
Paul L. Wood
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Fatty Acyl ◽  
Hydroxy Fatty Acids ◽  
Wax Esters ◽  
Hydroxyl Group ◽  
Cellular Functions ◽  
Health And Disease ◽  
Branched Chain

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.

scholarly journals Lipid metabolism. Evidence of a δ-oxidation pathway for saturated fatty acids

1969 ◽  
Vol 111 (4) ◽  
pp. 395-399 ◽  
Author(s):  
P. S. Dimick ◽  
N. J. Walker ◽  
Stuart Patton
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Saturated Fatty Acids ◽  
Radioactive Tracer ◽  
Hydroxy Fatty Acids ◽  
Lactating Goats ◽  
Total Milk ◽  
Milk Lipids ◽  
Active Intermediates

1. Specific radioactivities of milk triglyceride fatty acids and γ- and δ-hydroxy fatty acids were measured after the intramammary infusion of [1−14C]acetate, δ-hydroxy[1−14C]laurate and [1−14C]laurate as their sodium salts into fed lactating goats. 2. Net incorporations of the radioactive tracer into the total milk lipids were comparable, being 16, 17 and 21% of the label infused respectively. 3. The specific radioactivities of the C4–C8 fatty acids after [1−14C]acetate infusion were lower than those of the C10–C14 fatty acids. 4. After δ-hydroxy[1−14C]laurate administration the milk triglyceride fatty acids were labelled and their specific radioactivities were characterized by decreasing values with increasing chain length of the fatty acids, implicating C4 unit incorporation. 5. The γ- and δ-hydroxy fatty acids isolated after [1−14C]laurate infusion were highly labelled and the milk triglyceride fatty acids, other than laurate, exhibited a labelling pattern similar to that of the fatty acids derived from the radioactive δ-hydroxy fatty acid. 6. Evidence is presented for the existence of saturated fatty acid δ-oxidation in the mammary gland, in which the γ- and δ-hydroxy fatty acids are active intermediates.

scholarly journals Moose and Caribou as Novel Sources of Functional Lipids: Fatty Acid Esters of Hydroxy Fatty Acids, Diglycerides and Monoacetyldiglycerides

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 232 ◽  
Author(s):  
Thu Pham ◽  
Natalia Vidal ◽  
Charles Manful ◽  
Tiffany Fillier ◽  
Ryley Pumphrey ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Molecular Species ◽  
Hydroxy Fatty Acid ◽  
Inflammatory Diseases ◽  
Hydroxy Fatty Acids ◽  
Fatty Acid Esters ◽  
Acid Moiety ◽  
Molecular Species Composition ◽  
Acid Esters

Fatty acid esters of hydroxy fatty acids (FAHFA), diglycerides (DG) and monoacetyldiglycerides (MAcDG) are gaining interest as functional lipids in pharmaceuticals and functional food formulations for managing and treating metabolic or inflammatory diseases. Herein, we investigated whether the antler and/or meat of two Cervids (moose and caribou) are novel sources of FAHFA, DG and MAcDG. We observed FAHFA present in moose and caribou composed mainly of polyunsaturated families, and that the esterification occurred frequently at the C5-hydroxy fatty acid moiety, most noticeably arachidonic acid 5-hydroxyeicosatrienoic acid (ARA-5-HERA). Moose antler, caribou and moose meat also contained significant levels of both 1,2-DG and 1,3-DG lipids. The 1,3-DG molecular species consisted mainly of 16:0/18:1, 18:0/16:0, and 18:0/18:1. On the other hand, major 1,2-DG species consisted of DG 18:0/18:0, 16:0/16:0 and 18:1/18:1 molecular species with higher levels in the antler compared to the meat. The molecular species composition of MAcDG was very simple and consisted of 14:2/18:2/2:0, 16:0/18:2/2:0, 16:0/18:1/2:0 and 18:0/18:1/2:0 with the first species 14:2/18:2/2:0 predominating in the tip of moose antlers. Increasing access to and knowledge of the presence of these functional lipids in foods will enhance their intake in the diet with potential implications in improving personal and population health.

Incomplete fatty acid oxidation by ischemic heart: beta-hydroxy fatty acid production

1980 ◽  
Vol 239 (2) ◽  
pp. H257-H265 ◽  
Author(s):  
K. H. Moore ◽  
J. F. Radloff ◽  
F. E. Hull ◽  
C. C. Sweeley
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Acid Production ◽  
Hydroxy Fatty Acid ◽  
Oxygen Deficiency ◽  
Fatty Acid Content ◽  
Hydroxy Fatty Acids ◽  
Ischemic Heart ◽  
Fatty Acid Production ◽  
Exogenous Fatty Acid

A quantitative gas chromatography-mass spectrometry (GC/MS) method was developed to measure nanomolar quantities of long-chain saturated beta-hydroxy fatty acids (12, 14, 16, and 18 carbons long) produced by isolated ischemic heart. Only beta-hydroxymyristate (25-40 nmol/g dry) was found in fresh heart. Isolated rabbit heart perfused with fatty acid by the nonrecirculating Langendorff technique produced negligible beta-hydroxy fatty acids. Ischemic perfusion with 0.25-0.75 mM palmitate prompted heart beta-hydroxy fatty acid accumulation, beta-hydroxypalmitate greater than beta-hydroxystearate, up to 100 nmol x g dry-1 x 10 min-1. beta-Hydroxy fatty acid production was proportional to coronary effluent lactate-to pyruvate ratio, did not continue beyond 10 min of ischemia, was dependent on exogenous fatty acid, and was inhibited by coperfusion with 10 mM acetate. Reperfusion for 5-10 min dissipated accumulated beta-hydroxypalmitate. Hypoxic perfusion prompted beta-hydroxy fatty acid production comparable to that with severe ischemia. These data show that during oxygen deficiency heart fatty acid beta-oxidation is not only depressed but is also incomplete; beta-hydroxy fatty acyl intermediates accumulate and contribute to the increased intracellular fatty acid content characteristic of the ischemic myocardium.

scholarly journals Relationship between Hydroxy Fatty Acids and Prostaglandin E2 in Gingival Tissue

1998 ◽  
Vol 66 (12) ◽  
pp. 5805-5811 ◽  
Author(s):  
Frank Nichols ◽  
Baliram Maraj
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Hydroxy Fatty Acids ◽  
Gingival Tissue ◽  
Tissue Samples ◽  
Tissue Lipids ◽  
Complex Lipids ◽  
Bacterial Lipid ◽  
The Relationship

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.

Inactivation of Gram-Positive Bacteria by Novel Phenolic Branched-Chain Fatty Acids

2016 ◽  
Vol 80 (1) ◽  
pp. 6-14 ◽  
Author(s):  
XUETONG FAN ◽  
KAREN WAGNER ◽  
KIMBERLY J. B. SOKORAI ◽  
HELEN NGO
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxyl Group ◽  
Gram Negative Bacteria ◽  
Gram Positive ◽  
Gram Negative ◽  
Gram Positive Bacteria ◽  
Branched Chain Fatty Acids ◽  
Branched Chain ◽  
Chain Fatty Acids

ABSTRACT Novel phenolic branched-chain fatty acids (PBC-FAs) were evaluated for their antimicrobial properties against both gram-positive (Listeria innocua, Bacillus subtilis, Enterococcus faecium) and gram-negative (Escherichia coli, Salmonella Typhimurium, and Pseudomonas tolaasii) bacteria. In addition, PBC-FA derivatives, such as PBC-FA methyl ester mixture, methyl-branched fatty acid mixtures, and trimethylsilyl–PBC-FA methyl esters, were synthesized to study the structure activity relationship. Results showed that PBC-FAs were a potent antimicrobial against gram-positive bacteria with MICs of 1.8 to 3.6 μg/ml. The compounds were less effective against gram-negative bacteria. Derivatives of PBC-FAs and an equimolar mixture of oleic acid and phenol all had MICs above 233 μg/ml against both gram-positive and gram-negative bacteria. Comparison of antimicrobial activities of the PBC-FAs with those of the derivatives suggests that the carboxylic group in the fatty acid moiety and the hydroxyl group on the phenol moiety were responsible for the antimicrobial efficacy. Growth curves of L. innocua revealed that PBC-FAs prevented bacterial growth, while MBC-FAs only delayed the onset of rapid growth of L. innocua. Our results demonstrated that the novel PBC-FAs have potential for use as antimicrobials against gram-positive bacteria.

Fermentation of long-chain compounds by Torulopsis apicola. IV. Products from esters and hydrocarbons with 14 and 15 carbon atoms and from methyl palmitoleate

1968 ◽  
Vol 46 (9) ◽  
pp. 1523-1528 ◽  
Author(s):  
A. P. Tulloch ◽  
J. F. T. Spencer
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Carbon Chain ◽  
Hydroxy Fatty Acids ◽  
Hexadecenoic Acid ◽  
Hydroxy Acids ◽  
Chain Compounds ◽  
Long Chain ◽  
Direct Hydroxylation

Esters and hydrocarbons, containing 14 and 15 carbon atoms, are converted to the hydroxy fatty acid portions of glycosides by Torulopsis apicola in yields of 10–20%. When C-15 compounds are fermented, almost half of the hydroxy acids which are produced are 16-hydroxy C-17 acids. The carbon chain of the substrate is first lengthened by two carbon atoms and then hydroxylated. Direct hydroxylation also occurs, to a lesser extent, giving both 14-hydroxy- and 15-hydroxypentadecanoic acids. Similar results are obtained when C-14 compounds are used. Lengthening of the chain followed by hydroxylation gives rise to hydroxy C-16 acids and direct hydroxylation produces 13-hydroxy- and 14-hydroxytetradecanoic acids. Primary and secondary C-14 and C-15 alcohols were also isolated from the products of hydrocarbon fermentation (2.5–5 % yield). Methyl palmitoleate is converted to hydroxy fatty acids in yields of 40–70%, the major component of which is 16-hydroxy-cis-9-hexadecenoic acid.

scholarly journals AIG1 and ADTRP are endogenous hydrolases of fatty acid esters of hydroxy fatty acids (FAHFAs) in mice

2020 ◽  
Vol 295 (18) ◽  
pp. 5891-5905 ◽  
Author(s):  
Meric Erikci Ertunc ◽  
Bernard P. Kok ◽  
William H. Parsons ◽  
Justin G. Wang ◽  
Dan Tan ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Protein Profiling ◽  
Hydroxy Fatty Acids ◽  
Fatty Acid Esters ◽  
Genetic Studies ◽  
Health And Disease ◽  
Acid Esters

Fatty acid esters of hydroxy fatty acids (FAHFAs) are a newly discovered class of signaling lipids with anti-inflammatory and anti-diabetic properties. However, the endogenous regulation of FAHFAs remains a pressing but unanswered question. Here, using MS-based FAHFA hydrolysis assays, LC-MS–based lipidomics analyses, and activity-based protein profiling, we found that androgen-induced gene 1 (AIG1) and androgen-dependent TFPI-regulating protein (ADTRP), two threonine hydrolases, control FAHFA levels in vivo in both genetic and pharmacologic mouse models. Tissues from mice lacking ADTRP (Adtrp-KO), or both AIG1 and ADTRP (DKO) had higher concentrations of FAHFAs particularly isomers with the ester bond at the 9th carbon due to decreased FAHFA hydrolysis activity. The levels of other lipid classes were unaltered indicating that AIG1 and ADTRP specifically hydrolyze FAHFAs. Complementing these genetic studies, we also identified a dual AIG1/ADTRP inhibitor, ABD-110207, which is active in vivo. Acute treatment of WT mice with ABD-110207 resulted in elevated FAHFA levels, further supporting the notion that AIG1 and ADTRP activity control endogenous FAHFA levels. However, loss of AIG1/ADTRP did not mimic the changes associated with pharmacologically administered FAHFAs on extent of upregulation of FAHFA levels, glucose tolerance, or insulin sensitivity in mice, indicating that therapeutic strategies should weigh more on FAHFA administration. Together, these findings identify AIG1 and ADTRP as the first endogenous FAHFA hydrolases identified and provide critical genetic and chemical tools for further characterization of these enzymes and endogenous FAHFAs to unravel their physiological functions and roles in health and disease.

scholarly journals Succinct synthesis of saturated hydroxy fatty acids andin vitroevaluation of all hydroxylauric acids on FFA1, FFA4 and GPR84

MedChemComm ◽  
2017 ◽  
Vol 8 (6) ◽  
pp. 1360-1365 ◽  
Author(s):  
Mads Holmgaard Kaspersen ◽  
Laura Jenkins ◽  
Julia Dunlop ◽  
Graeme Milligan ◽  
Trond Ulven
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Hydroxy Fatty Acids

A concise synthetic protocol enables rapid receptor screening of hydroxy fatty acid.

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