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 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 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 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.

scholarly journals Polyenoic very-long-chain fatty acids mobilize intracellular calcium from a thapsigargin-insensitive pool in human neutrophils. The relationship between Ca2+ mobilization and superoxide production induced by long- and very-long-chain fatty acids

1995 ◽  
Vol 311 (2) ◽  
pp. 689-697 ◽  
Author(s):  
S J Hardy ◽  
B S Robinson ◽  
A Ferrante ◽  
C S T Hii ◽  
D W Johnson ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Chain Length ◽  
Carbon Chain ◽  
Superoxide Production ◽  
Human Neutrophils ◽  
Carbon Chain Length ◽  
Long Chain Fatty Acids ◽  
Long Chain ◽  
Chain Fatty Acids

Fatty acids with more than 22 carbon atoms (very-long-chain fatty acids; VLCFAs) are normal cellular components that have been implicated in the pathophysiology of a number of peroxisomal disorders. To date, however, essentially nothing is known regarding their biological activities. Ca2+ mobilization is an important intracellular signalling system for a variety of agonists and cell types. Given that several polyunsaturated long-chain fatty acids mobilize intracellular Ca2+ and that we have postulated that the VLCFAs may be involved in signal transduction, we examined whether the tetraenoic VLCFA induced Ca2+ mobilization in human neutrophils. We report that fatty acid-induced intracellular Ca2+ mobilization declined for fatty acid species of more than 20 carbon atoms, but increased again as the carbon chain length approached 30. This Ca2+ mobilization occurred independently of inositol 1,4,5-triphosphate production and protein kinase C translocation and involved both the release of Ca2+ from the intracellular stores and changes to the influx or efflux of the ion. We further observed that triacontatetraenoic acid [30:4(n-6)] mobilized Ca2+ from a thapsigargin-insensitive intracellular pool distinct from the thapsigargin-sensitive pools affected by arachidonic acid [20:4(n - 6)] or N-formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP). 20:4 (n - 6) induced strong superoxide production (chemiluminescence) which was inhibited by thapsigargin pretreatment. In contrast, fatty acid-induced superoxide production progressively declined as the carbon chain length increased beyond 20-22 carbon atoms. Further studies suggested that the thapsigargin-insensitive Ca2+ mobilization elicited by 30:4 (n - 6) was not related to oxyradical formation, while the thapsigargin-sensitive Ca2+ mobilization induced by 20:4 (n - 6) may be involved in the initiation but not necessarily the maintenance of superoxide production. In conclusion, this is the first report to demonstrate a biological activity for the VLCFA and indicates that 30:4 (n - 6) influences second messenger systems in intact cells that differ from those affected by long-chain fatty acids such as 20:4 (n - 6).

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.

THE FERMENTATION OF LONG-CHAIN COMPOUNDS BY TORULOPSIS MAGNOLIAE: I. STRUCTURES OF THE HYDROXY FATTY ACIDS OBTAINED BY THE FERMENTATION OF FATTY ACIDS AND HYDROCARBONS

1962 ◽  
Vol 40 (7) ◽  
pp. 1326-1338 ◽  
Author(s):  
A. P. Tulloch ◽  
J. F. T. Spencer ◽  
P. A. J. Gorin
Keyword(s):  
Fatty Acids ◽  
Carbon Atom ◽  
Chain Length ◽  
Hydroxy Fatty Acid ◽  
Hydroxyl Group ◽  
Fatty Esters ◽  
Degree Of Unsaturation ◽  
Chain Compounds ◽  
Chain Lengths ◽  
Long Chain

The yield of extracellular glycolipid produced by Torulopsis magnoliae is increased three-to five-fold by the addition of suitable compounds to the growing culture. The supplement, which can be a long-chain acid, ester, hydrocarbon, or glyceride, is hydroxylated and converted to hydroxy fatty acid sophorosides. Fatty esters of all chain lengths from C16 to C22, including several unsaturated esters, and even-numbered hydrocarbons from C16 to C24 are readily fermented. Shorter-chain compounds are used poorly or not at all. With compounds of 16 to 18 carbon atoms, hydroxylation occurs at the terminal or penultimate carbon atom, depending on degree of unsaturation and chain length. Substrates of more than 18 carbon atoms are mainly reduced in chain length by one or more two-carbon units and hydroxylated, giving C17 or C18 acids with the hydroxyl group on the penultimate carbon atom. The various enzymic reactions which occur during the fermentation are discussed.

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.

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