Lipid Geometrical Isomerism: From Chemistry to Biology and Diagnostics

Chatgilialoglu, Chryssostomos; Ferreri, Carla; Melchiorre, Michele; Sansone, Anna; Torreggiani, Armida

doi:10.1021/cr4002287

Cited by 171 publications

(201 citation statements)

References 282 publications

Supporting

Mentioning

197

Contrasting

Order By: Relevance

“…The dietary TFA found in biological membranes can induce oxidative stress. Additionally, TFA can be formed in vivo by oxidative stress since ROS can react with unsaturated fatty acids to cause either a cis-trans isomerization [16], or a peroxidation reaction yielding to F 2 -isoPs. These two pathways most likely explain the link between TFA and F 2 -isoPs in the present report.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

F2-isoprostanes are correlated with trans fatty acids in the plasma of pregnant women

LaRose¹,

Julien

Fraser

et al. 2014

Prostaglandins, Leukotrienes and Essential Fatty Acids

View full text Add to dashboard Cite

We hypothesized that the mild physiological oxidative stress present during pregnancy could increase both, plasma F 2 -isoprostanes (F 2 -isoPs) by lipid oxidation and trans fatty acids (TFA) through cis-trans isomerization respectively. Plasma samples collected at 12-18 weeks (MIROS cohort; n=65) and 38-41 weeks of pregnancy (CHUL cohort; n = 21) were subjected to alkaline hydrolysis followed by liquid-liquid extraction in order to extract total F 2 -isoPs for quantification by HPLC-MS/MS. Several positive correlations were found between F 2 -isoPs and TFA, measured by GC-FID in plasma phospholipids, such as 6t-18:1, 9t-18:1 and 9t,12c-18:2 (r > 0.306; p < 0.045). Despite its low level, the 9t,12c-18:2 trans isomer, known to be associated to cardiovascular diseases, showed the most significant correlations with F 2 -isoPs. No correlation was observed between F 2 -isoPs and 9t-16:1 or 11t-18:1. In summary, this study suggests either a concomitant phenomenon or a competition between lipid peroxidation and cis-trans isomerisation of the cis precursor fatty acid in vivo during pregnancy.

show abstract

Section: Discussionmentioning

confidence: 99%

“…The mechanism proposed for cis-trans isomerisation is the action of either the thiyl or the nitrogen dioxide radicals on cis fatty acids [14][15][16]. The latter phenomenon was shown to occur in rats that were fed only with cis-fatty acids, then were exposed to carbon tetrachloride, an agent causing an oxidative stress [17].…”

Section: Introductionmentioning

confidence: 99%

F2-isoprostanes are correlated with trans fatty acids in the plasma of pregnant women

LaRose¹,

Julien

Fraser

et al. 2014

Prostaglandins, Leukotrienes and Essential Fatty Acids

View full text Add to dashboard Cite

show abstract

“…In any BMI group there was a strong unbalance of SFA/MUFA ratios compared to the control values ( Table 3). The evidenced excess of SFA was an index of increased membrane rigidity, consequent altered permeability and functionality, with possible metabolic and cardiovascular risks [13,15,19]. These results at least allow correcting the quality of food, limiting the intake Percentage (%) refers to the number of affected subjects per each group of PAR-PARP levels.…”

Section: Membrane Fatty Acid Analysismentioning

confidence: 99%

“…in contents of saturated (SFA), mono-(MUFA) and polyunsaturated (PUFA) fatty acids. Release of PUFA from membrane phospholipids triggers some physiological events [13][14][15]. Therefore the knowledge of the membrane status can be very important for the evaluation of the overall metabolic functioning [16].…”

Section: Introductionmentioning

confidence: 99%

Auto-Modification of Poly (ADP-Ribose) Polymerase and Membrane Lipid Composition as Diagnostic Tools to Measure the Physio-Pathological State of the Cell

Bianchi¹,

Ruggiero²,

Formisano³

et al. 2014

J Microb Biochem Technol

View full text Add to dashboard Cite

Poly(ADPribosyl)ation, catalysed by poly(ADP-ribose)polymerases, affects many cellular events and has a recognized epigenetic role. Nuclear poly(ADP-ribose)polymerases 1 and 2 are hyper activated by DNA strandbreaks. They auto-modify with large polymers of ADP-ribose and recruit DNA repair proteins. The more the DNA strand-breaks, the more poly(ADP-ribose) polymerase modifies itself.On the other hand, dietary lipids can be signaling molecules, lead to pro-(ω6)/ anti-(ω3) inflammatory compounds, and be included in biomembranes, good biomarkers of their unbalance.Here, we report the results obtained from an epidemiological study to establish whether the combination of two different analyses, i.e. detecting auto-modified poly (ADP-ribose) polymerase levels and analyzing erythrocyte membrane fatty acid composition, might help to monitor the physio-pathological state of the cell, and to correlate with lifestyle, diet or diseases. The two analyses were carried blindly on 70 subjects undergoing endoscopy. They were first interviewed, to collect anamnesis and clinical data, if present. Lymphocytes and erythrocytes were prepared from venous blood to assay poly (ADP-ribose) polymerase auto modification and membrane fatty acid content, respectively. The results were statistically evaluated. The measure of poly (ADP-ribose) polymerase automodification confirmed that its levels correlate with DNA damage extent, within the same pathology, and allowed to monitor the clinical activity of the disease, depending on ongoing therapeutic/surgical treatment. Membrane fat profile was able to evidence unbalance of lipids linked to both diet/lifestyle and inflammatory states leading to diseases. Both analyses provide possible biomarkers for sensible, non-invasive and routine monitoring.

show abstract

“…[2][3][4][5][6] Some trans fatty acid residues found in living organisms can only be formed through an endogenous transformation of the natural occurring cis conformation, and their presence has been correlated with radical stress under physiological and pathological processes. [7][8][9] Several free radicals, including the biologically relevant thiyl radicals (RS•) 10 and nitrogen dioxide (•NO 2 ), 8 are known to isomerize double bonds. Scheme 1 shows the reaction mechanism, involving reversible addition of a radical X• to the double bond to form a radical adduct (A•).…”

Section: Introductionmentioning

confidence: 99%

Biomimetic chemistry on the protection of cis phospholipid from the thiyl radical isomerization by common antioxidants

Lykakis¹,

Ferreri²,

Chatgilialoglu³

2015

Arkivoc

Self Cite

View full text Add to dashboard Cite

Dedicated to Prof. Michael Orfanopoulos on the occasion of his 67th birthday and retirement, and for being a splendid teacher, scientist and friend DOI: http://dx.doi.org/10.3998/ark.5550190.p008.984 AbstractIn this paper the evaluation of cis phospholipids geometry protection from the thiyl radical isomerization in the presence of common antioxidants is studied. Thus, large unilamellar vesicles (LUVs) of glycerophospholipids containing oleate moieties were used as biomimetic model to demonstrate that hydrophilic ascorbic acid and urate, and hydrophobic all-trans retinol acetate and α-tocopherol, are able to inhibit cis-trans isomerization from the thiyl radicals that are known to react as efficient isomerizing species. The synergistic effect obtained by a mix of the hydrophilic and hydrophobic antioxidants at in vivo concentrations is also proved to exert an extraordinary protection for the integrity of cis lipid geometry.

show abstract

Lipid Geometrical Isomerism: From Chemistry to Biology and Diagnostics

Cited by 171 publications

References 282 publications

F2-isoprostanes are correlated with trans fatty acids in the plasma of pregnant women

F2-isoprostanes are correlated with trans fatty acids in the plasma of pregnant women

Auto-Modification of Poly (ADP-Ribose) Polymerase and Membrane Lipid Composition as Diagnostic Tools to Measure the Physio-Pathological State of the Cell

Biomimetic chemistry on the protection of cis phospholipid from the thiyl radical isomerization by common antioxidants

Contact Info

Product

Resources

About