scholarly journals Cholesteryl esters of ω-( O -acyl)-hydroxy fatty acids in vernix caseosa

2017 ◽  
Vol 58 (8) ◽  
pp. 1579-1590 ◽  
Author(s):  
Aneta Kalužíková ◽  
Vladimír Vrkoslav ◽  
Eva Harazim ◽  
Michal Hoskovec ◽  
Richard Plavka ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Hydroxy Fatty Acids ◽  
Cholesteryl Esters ◽  
Vernix Caseosa

scholarly journals Incorporation of lipoxygenase products into cholesteryl esters by acyl-CoA:cholesterol acyltransferase in cholesterol-rich macrophages

1988 ◽  
Vol 256 (3) ◽  
pp. 807-814 ◽  
Author(s):  
S N Mathur ◽  
E Albright ◽  
F J Field
Keyword(s):  
Fatty Acids ◽  
Foam Cell ◽  
Fatty Acyl ◽  
Hydroxy Fatty Acids ◽  
Cholesteryl Esters ◽  
Acat Activity ◽  
Lipoxygenase Products ◽  
First Time ◽  
Total Membrane ◽  
Cholesteryl Ester Accumulation

Macrophages which were incubated with acetylated low-density lipoproteins, resulting in cholesteryl ester accumulation, incorporated the monohydroxyeicosatetraenoic acids (5-, 15-, and 12-HETEs) into cholesteryl esters. The esterification of these hydroxy fatty acids to cholesterol by total membrane preparations of cholesterol-rich macrophages was dependent on the synthesis of the fatty acyl-CoA derivative, and was catalysed by acyl-CoA:cholesterol acyltransferase (ACAT). Stimulation of membrane ACAT activity by 25-hydroxycholesterol increased the synthesis of cholesteryl 12-HETE by 40%. In contrast, inhibiting ACAT activity by progesterone and compound 58-035 decreased cholesteryl 12-HETE production by 60% and 90% respectively. Although 5-, 15- and 12-HETE were esterified to cholesterol by ACAT, these monohydroxy fatty acids were less optimal as substrates compared with oleic acid or arachidonic acid. The hydrolysis and release of 12-HETE and the other monohydroxyeicosatetraenoic acids from intracellular cholesteryl esters and phospholipids occurred at a faster rate than for the more conventional fatty acids, oleate and arachidonate. Cholesteryl esters which contain hydroxy fatty acids therefore provide only a transient storage for lipoxygenase products, as these fatty acids are released into the medium as readily as hydroxy fatty acids found in phospholipids and triacylglycerols. The data provide evidence, for the first time, of an ACAT-dependent esterification of the lipoxygenase products 5-, 15- and 12-HETEs to cholesterol in the macrophage-derived foam cell. The channelling of these monohydroxy fatty acids to cholesteryl esters provides a mechanism which can alter the amount of lipoxygenase products incorporated into cellular phospholipids, thus averting deleterious changes to cell membranes. ACAT, by catalysing the esterification of monohydroxyeicosatetraenoic acids to cholesterol, could play a key role in regulating the amount of lipoxygenase products in the pericellular space of the cholesterol-enriched macrophage.

scholarly journals Occurrence of 2-hydroxy fatty acids in animal tissues

1963 ◽  
Vol 4 (2) ◽  
pp. 139-143 ◽  
Author(s):  
Yasuo Kishimoto ◽  
Norman S. Radin
Keyword(s):  
Fatty Acids ◽  
Hydroxy Fatty Acids ◽  
Animal Tissues

scholarly journals Optimization and Engineering of a Self-Sufficient CYP102 Enzyme from Bacillus amyloliquefaciens towards Synthesis of In-Chain Hydroxy Fatty Acids

Catalysts ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 665
Author(s):  
Li Zong ◽  
Yan Zhang ◽  
Zhengkang Shao ◽  
Yingwu Wang ◽  
Zheng Guo ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Palmitic Acid ◽  
Bacillus Amyloliquefaciens ◽  
Catalytic Domain ◽  
Hydroxy Fatty Acids ◽  
Saturation Mutagenesis ◽  
Long Chain Fatty Acids ◽  
Medical Field ◽  
Biotransformation Process ◽  
Total Product

Cytochrome P450 (CYP) mediated enzymatic hydroxylation of fatty acids present a green alternative to chemical synthesis of hydroxy fatty acids (HFAs), which are high-value oleochemicals with various uses in materials industry and medical field. Although many CYPs require the presence of additional reductase proteins for catalytic activity, self-sufficient CYPs have their reductase partner naturally fused into their catalytic domain, leading to a greatly simplified biotransformation process. A recently discovered self-sufficient CYP, BAMF2522 from Bacillus amyloliquefaciens DSM 7, exhibits novel regioselectivity by hydroxylating in-chain positions of palmitic acid generating ω-1 to ω-7 HFAs, a rare regiodiversity profile among CYPs. Besides, F89I mutant of BAMF2522 expanded hydroxylation up to ω-9 position of palmitic acid. Here, we further characterize this enzyme by determining optimum temperature and pH as well as thermal stability. Moreover, using extensive site-directed and site-saturation mutagenesis, we obtained BAMF2522 variants that demonstrate greatly increased regioselectivity for in-chain positions (ω-4 to ω-9) of various medium to long chain fatty acids. Remarkably, when a six-residue mutant was reacted with palmitic acid, 84% of total product content was the sum of ω-7, ω-8 and ω-9 HFA products, the highest in-chain selectivity observed to date with a self-sufficient CYP. In short, our study demonstrates the potential of a recently identified CYP and its mutants for green and sustainable production of a variety of in-chain hydroxy enriched HFAs.

Gas chromatographic separation of cholesteryl esters of fatty acids of different degrees of unsaturation

Lipids ◽  
1977 ◽  
Vol 12 (2) ◽  
pp. 228-232 ◽  
Author(s):  
Toru Takagi ◽  
Akira Sakai ◽  
Yutaka Itabashi ◽  
Kenji Hayashi
Keyword(s):  
Fatty Acids ◽  
Chromatographic Separation ◽  
Cholesteryl Esters ◽  
Gas Chromatographic Separation
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