Composition of long-chain bases in sphingomyelin of the guinea pig Harderian gland

1990 ◽  
Vol 68 (1) ◽  
pp. 154-160 ◽  
Author(s):  
E. Yasugi ◽  
T. Kasama ◽  
M. Shibahara ◽  
Y. Seyama
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Guinea Pig ◽  
High Performance ◽  
Minor Component ◽  
Harderian Gland ◽  
Hydroxy Acids ◽  
Branched Fatty Acids ◽  
Methyl Branched Fatty Acids ◽  
Long Chain

Sphingomyelin from the guinea pig Harderian gland was isolated and characterized. The purified sphingomyelin gave a broad spot on thin-layer chromatography. The fatty acid composition of the whole sphingomyelin was 71% nonhydroxy acids and 29% 2-hydroxy acids. Methyl-branched fatty acids were only 2% of the total acids. The long-chain bases were composed of straight-chain sphingenines (50%) and sphinganines (6%). Methyl-branched long-chain bases were 44% of the bases. The sphingomyelin was further separated into four fractions (I, II, III, IV) by high-performance liquid chromatography. The ratio of fractions I, II, III, and IV was approximately 2:5:2:1, respectively. The fatty acids of fractions I and II consisted of nonhydroxy acids and those of fractions III and IV were 2-hydroxy acids. The long-chain bases of fractions I and III were sphinganines including 10-, 9-, and 8-methylsphinganines and anteiso-sphinganines. These methyl-branched bases occupied about 70% of the total sphinganines. The long-chain bases of fractions II and IV consisted of sphingenines. The methyl-branched unsaturated bases were only 30% of the total sphingenines, all in the anteiso-form. Thus, the sphingomyelin obtained from guinea pig Harderian gland had complex compositions of fatty acids and long-chain bases, and half the number of long-chain bases had methyl branches. The methyl-branched fatty acids were only a minor component. These characteristics are similar to those of cerebrosides isolated from the same source.Key words: long chain base, fatty acid, sphingomyelin, guinea pig, Harderian gland.

scholarly journals Novel identification of the free fatty acid receptor FFAR1 that promotes contraction in airway smooth muscle

2015 ◽  
Vol 309 (9) ◽  
pp. L970-L982 ◽  
Author(s):  
Kentaro Mizuta ◽  
Yi Zhang ◽  
Fumiko Mizuta ◽  
Hiroshi Hoshijima ◽  
Toshiya Shiga ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Smooth Muscle ◽  
Fatty Acid ◽  
Free Fatty Acid ◽  
Guinea Pig ◽  
Free Fatty Acids ◽  
Airway Smooth Muscle ◽  
Muscle Tone ◽  
Fiber Formation ◽  
Long Chain

Obesity is one of the major risk factors for asthma. Previous studies have demonstrated that free fatty acid levels are elevated in the plasma of obese individuals. Medium- and long-chain free fatty acids act as endogenous ligands for the free fatty acid receptors FFAR1/GPR40 and FFAR4/GPR120, which couple to Gq proteins. We investigated whether FFAR1 and FFAR4 are expressed on airway smooth muscle and whether they activate Gq-coupled signaling and modulate airway smooth muscle tone. We detected the protein expression of FFAR1 and FFAR4 in freshly dissected native human and guinea pig airway smooth muscle and cultured human airway smooth muscle (HASM) cells by immunoblotting and immunohistochemistry. The long-chain free fatty acids (oleic acid and linoleic acid) and GW9508 (FFAR1/FFAR4 dual agonist) dose-dependently stimulated transient intracellular Ca2+ concentration ([Ca2+]i) increases and inositol phosphate synthesis in HASM cells. Downregulation of FFAR1 or FFAR4 in HASM cells by small interfering RNA led to a significant inhibition of the long-chain free fatty acids-induced transient [Ca2+]i increases. Oleic acid, linoleic acid, or GW9508 stimulated stress fiber formation in HASM cells, potentiated acetylcholine-contracted guinea pig tracheal rings, and attenuated the relaxant effect of isoproterenol after an acetylcholine-induced contraction. In contrast, TUG-891 (FFAR4 agonist) did not induce the stress fiber formation or potentiate acetylcholine-induced contraction. These results suggest that FFAR1 is the functionally dominant free fatty acid receptor in both human and guinea pig airway smooth muscle. The free fatty acid sensors expressed on airway smooth muscle could be an important modulator of airway smooth muscle tone.

scholarly journals Active synthesis of C24:5, n-3 fatty acid in retina

1996 ◽  
Vol 316 (3) ◽  
pp. 859-864 ◽  
Author(s):  
N. P. ROTSTEIN ◽  
G. L. PENNACCHIOTTI ◽  
H. SPRECHER ◽  
M. I. AVELDAÑO
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Minor Component ◽  
Major Fatty Acid ◽  
Active Synthesis ◽  
Fatty Acid Constituent ◽  
A Minor ◽  
Long Chain ◽  
Pufa Metabolism ◽  
Active Formation

The formation of 14C-labelled long-chain and very-long-chain (n-3) pentaenoic and hexaenoic fatty acids was studied in bovine retina by following the metabolism of [14C]docosapentaenoate [C22:5, n-3 fatty acid (22:5 n-3)], [14C]docosahexaenoate (22:6 n-3), and [14C]acetate. With similar amounts of 22:5 n-3 and 22:6 n-3 as substrates, the former was actively transformed into 24:5 n-3, whereas the latter was virtually unmodified. Labelled 24:5, 26:5, 24:6 and 22:6 were formed from [1-14C]22:5 n-3, showing that pentaenoic fatty acids including 24:5 n-3 can be elongated and desaturated within the retina. When retinal microsomes were incubated with [1-14C]22:5 n-3, 24:5 n-3 was the only fatty acid formed. In retinas incubated with [14C]acetate, 24:5 n-3 was the most highly labelled fatty acid among the polyenes synthesized, 24:6 n-3 being a minor product. Such selectivity in the elongation of two fatty acids identical in length, 22:5 n-3 and 22:6 n-3, despite the fact that 22:5 is a minor and 22:6 a major fatty acid constituent of retina, suggests that the active formation of 24:5 n-3 plays a key role in n-3 polyunsaturated fatty acid (PUFA) metabolism. This compound might give rise to even longer pentaenes via elongation, and to the major PUFAs of retina, 22:6 n-3, by 6-desaturation and chain shortening. Of all retinal lipids, a minor component, triacylglycerol (TG), incorporated the largest amounts of [14C]22:5 and 22:6. TG also concentrated most of the [14C]24:5 formed in retina, whether from [14C]22:5 n-3 or from [14C]acetate, suggesting an important role for this lipid in supporting PUFA metabolism and the synthesis of 22:6 n-3.

Self-assembly of long chain fatty acids: effect of a methyl branch

2014 ◽  
Vol 16 (33) ◽  
pp. 17869-17882 ◽  
Author(s):  
Jonathan F. D. Liljeblad ◽  
Eric Tyrode ◽  
Esben Thormann ◽  
Ann-Claude Dublanchet ◽  
Gustavo Luengo ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Self Assembly ◽  
Molecular Conformation ◽  
Long Chain Fatty Acids ◽  
Methyl Branch ◽  
Straight Chain ◽  
Branched Fatty Acids ◽  
Methyl Branched Fatty Acids ◽  
Long Chain ◽  
Chain Fatty Acids

The morphology and molecular conformation of monolayers of straight chain and methyl-branched fatty acids have been investigated by VSFS and AFM, revealing domains in the latter case, due to inverse micellar packing constraints.

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 Production of 10-methyl branched fatty acids in yeast

2021 ◽  
Vol 14 (1) ◽  
Author(s):  
Hannah G. Blitzblau ◽  
Andrew L. Consiglio ◽  
Paulo Teixeira ◽  
Donald V. Crabtree ◽  
Shuyan Chen ◽  
...  
Keyword(s):  
Fatty Acids ◽  
High Performance ◽  
Large Scale ◽  
Unsaturated Fatty Acids ◽  
Acyl Chain ◽  
Efficient Production ◽  
Scale Production ◽  
Branched Fatty Acids ◽  
Large Scale Production ◽  
Methyl Branched Fatty Acids

Abstract Background Despite the environmental value of biobased lubricants, they account for less than 2% of global lubricant use due to poor thermo-oxidative stability arising from the presence of unsaturated double bonds. Methyl branched fatty acids (BFAs), particularly those with branching near the acyl-chain mid-point, are a high-performance alternative to existing vegetable oils because of their low melting temperature and full saturation. Results We cloned and characterized two pathways to produce 10-methyl BFAs isolated from actinomycetes and γ-proteobacteria. In the two-step bfa pathway of actinomycetes, BfaB methylates Δ9 unsaturated fatty acids to form 10-methylene BFAs, and subsequently, BfaA reduces the double bond to produce a fully saturated 10-methyl branched fatty acid. A BfaA-B fusion enzyme increased the conversion efficiency of 10-methyl BFAs. The ten-methyl palmitate production (tmp) pathway of γ-proteobacteria produces a 10-methylene intermediate, but the TmpA putative reductase was not active in E. coli or yeast. Comparison of BfaB and TmpB activities revealed a range of substrate specificities from C14-C20 fatty acids unsaturated at the Δ9, Δ10 or Δ11 position. We demonstrated efficient production of 10-methylene and 10-methyl BFAs in S. cerevisiae by secretion of free fatty acids and in Y. lipolytica as triacylglycerides, which accumulated to levels more than 35% of total cellular fatty acids. Conclusions We report here the characterization of a set of enzymes that can produce position-specific methylene and methyl branched fatty acids. Yeast expression of bfa enzymes can provide a platform for the large-scale production of branched fatty acids suitable for industrial and consumer applications.

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