Metabolism of trans fatty acid isomers

Sébédio, Jean‐Louis; Christie, William W.

doi:10.1533/9780857097873.163

Cited by 7 publications

(9 citation statements)

References 103 publications

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“…Figure 3 (B) shows the dose profiles of methyl oleate disappearance in LUVs in the absence (dashed line), as well as in the presence of 60 µM of UH 3 at different pH values. The inhibition of the isomerization process owing to presence of UH 3 is similar to that observed with previous hydrophilic antioxidant AH 2 . However, the substantially low inhibition effect of urate on the cis-trans lipid isomerization observed at pH 3, demonstrated that the protonated form of UH 3 (pK a1 5.4 and pK a2 9.8 for the UH 3 ) 38,39 is less active than the corresponding deprotonated form UH 2 -which predominates at pH 7 and 9.…”

Section: Resultssupporting

confidence: 88%

“…Geometric isomerism has become a topic of research involving several disciplines, such as microbiology, chemistry, biochemistry, pharmacology, nutrition, and medicine. [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.…”

Section: Introductionmentioning

confidence: 99%

“…In fact, trans-fatty acids can be taken from the diet, particularly through food like meat, milk, and partially hydrogenated fats and oils. 2,10,19 Based on the efficiency of the thiyl radicalcatalyzed cis-trans isomerization, it was demonstrated that trans-phospholipids could be also formed in vivo under cellular stress. [12][13][14] The protection of the cis geometry is crucial, owing to the importance of keeping favourable properties of cell membranes deriving from the fluidity contribution by the bent unsaturated lipid structures.…”

Section: Introductionmentioning

confidence: 99%

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

Lykakis¹,

Ferreri²,

Chatgilialoglu³

2015

Arkivoc

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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.

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Section: Resultssupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

Lykakis¹,

Ferreri²,

Chatgilialoglu³

2015

Arkivoc

View full text Add to dashboard Cite

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“…In the last two decades the occurrence of trans lipids has been studied in two main contexts: (a) dietary supplementation, as exogenous source of trans lipids in foods that have undergone industrial processes like partial hydrogenation [ 11 ] and deodorization [ 12 ]; and (b) endogenous formation by cellular stress conditions which give rise to sulfur centered radicals, highly specific and reactive for the cis - trans double bond isomerization of biological lipids ( Figure 1 D) [ 6 , 8 , 13 , 14 ]. The isomerization process has been also connected with free radical formation generated in cells by thiol-metal complexes, such as those involved in antitumoral drug mechanisms.…”

Section: Introductionmentioning

confidence: 99%

trans-Double Bond-Containing Liposomes as Potential Carriers for Drug Delivery

et al. 2017

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The use of liposomes has been crucial for investigations in biomimetic chemical biology as a membrane model and in medicinal chemistry for drug delivery. Liposomes are made of phospholipids whose biophysical characteristics strongly depend on the type of fatty acid moiety, where natural unsaturated lipids always have the double bond geometry in the cis configuration. The influence of lipid double bond configuration had not been considered so far with respect to the competence of liposomes in delivery. We were interested in evaluating possible changes in the molecular properties induced by the conversion of the double bond from cis to trans geometry. Here we report on the effects of the addition of trans-phospholipids supplied in different amounts to other liposome constituents (cholesterol, neutral phospholipids and cationic surfactants), on the size, ζ-potential and stability of liposomal formulations and on their ability to encapsulate two dyes such as rhodamine B and fluorescein. From a biotechnological point of view, trans-containing liposomes proved to have different characteristics from those containing the cis analogues, and to influence the incorporation and release of the dyes. These results open new perspectives in the use of the unnatural lipid geometry, for the purpose of changing liposome behavior and/or of obtaining molecular interferences, also in view of synergic effects of cell toxicity, especially in antitumoral strategies.

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“…The main dietary source of trans fatty acids has been partially hydrogenated vegetable oil (PHVO), which can contain up to 60% trans fatty acids. The trans fatty acids in PHVO are mainly in the form of trans -octadecenoic acid ( t -18:1), representing 90–95% of total trans fatty acids in PHVO [3] . Among these, t 9-18:1 (elaidic acid) and t 10-18:1 are typically the first and second major isomers, making up on average about 28% and 21% of total t- 18:1 respectively [4] .…”

Section: Introductionmentioning

confidence: 99%

A trans 10-18:1 enriched fraction from beef fed a barley grain-based diet induces lipogenic gene expression and reduces viability of HepG2 cells

Vahmani

Meadus

Silva

et al. 2016

Biochemistry and Biophysics Reports

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Beef fat is a natural source of trans (t) fatty acids, and is typically enriched with either t10-18:1 or t11-18:1. Little is known about the bioactivity of individual t-18:1 isomers, and the present study compared the effects of t9-18:1, cis (c)9-18:1 and trans (t)-18:1 fractions isolated from beef fat enriched with either t10-18:1 (HT10) or t11-18:1 (HT11). All 18:1 isomers resulted in reduced human liver (HepG2) cell viability relative to control. Both c9-18:1 and HT11were the least toxic, t9-18:1had dose response increased toxicity, and HT10 had the greatest toxicity (P<0.05). Incorporation of t18:1 isomers was 1.8–2.5 fold greater in triacylglycerol (TG) than phospholipids (PL), whereas Δ9 desaturation products were selectively incorporated into PL. Culturing HepG2 cells with t9-18:1 and HT10 increased (P<0.05) the Δ9 desaturation index (c9–16:1/16:0) compared to other fatty acid treatments. HT10 and t9-18:1 also increased expression of lipogenic genes (FAS, SCD1, HMGCR and SREBP2) compared to control (P<0.05), whereas c9-18:1 and HT11 did not affect the expression of these genes. Our results suggest effects of HT11 and c9-18:1 were similar to BSA control, whereas HT10 and t-9 18:1 (i.e. the predominant trans fatty acid isomer found in partially hydrogenated vegetable oils) were more cytotoxic and led to greater expression of lipogenic genes.

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Metabolism of trans fatty acid isomers

Cited by 7 publications

References 103 publications

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

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

trans-Double Bond-Containing Liposomes as Potential Carriers for Drug Delivery

A trans 10-18:1 enriched fraction from beef fed a barley grain-based diet induces lipogenic gene expression and reduces viability of HepG2 cells

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